Organic Synthesis

Organic Synthesis: State of the Art 2011-2013 is a convenient, concise reference that summarizes the most important current developments in organic synthesis, from functional group transformations to complex natural product synthesis. The fifth volume in the esteemed State of the Art series, the book compiles two years' worth of Douglass Taber's popular weekly column Organic Chemistry Highlights. The series is an invaluable resource, leading chemists quickly and easily to the most significant developments in the field.The book is logically divided into two sections: the first section focuses on specific topics in organic synthesis, such as C-N Ring Construction and Carbon-Carbon Bond Formation. Each topic is presented using the most significant publications within those areas of research. The journal references are included in the text. The second section focuses on benchmark total syntheses, with an analysis of the strategy for each, and discussions of pivotal transformations.Synthetic organic chemistry is a complex and rapidly growing field, with additional new journals appearing almost every year. Staying abreast of recent research is a daunting undertaking. This book is an ideal tool for both practicing chemists and students, offering a rich source of information and suggesting fruitful pathways for future investigation.

ContentsPrefaceOrganic Functional Group Interconversion and Protection1. Functional Group Transformations organic-chemistry.org/Highlights/2012/14May.shtm May 14, 20122. Functional Group Interconversion organic-chemistry.org/Highlights/2012/22October. shtm October 22, 20123. Functional Group Interconversion organic-chemistry.org/Highlights/2013/13May.shtm May 13, 20134. Functional Group Interconversion organic-chemistry.org/Highlights/2013/28October. shtm October 28, 20135. Reduction and Oxidation organic-chemistry.org/Highlights/2012/21May.shtm May 21, 20126. Functional Group Oxidation and Reduction organic-chemistry.org/Highlights/2012/12November .shtm November 12, 20127. Functional Group Oxidation organic-chemistry.org/Highlights/2013/20May.shtm May 20, 20138. Functional Group Reduction organic-chemistry.org/Highlights/2013/27May.shtm May 27, 20139. Functional Group Protection organic-chemistry.org/Highlights/2012/28May.shtm May 28, 201210. Functional Group Protection organic-chemistry.org/Highlights/2012/29October. shtm October 29, 201211. Functional Group Protection organic-chemistry.org/Highlights/2013/10June.sht m June 12, 201312. Functional Group Protection organic-chemistry.org/Highlights/2013/11November .shtm November 11, 2013Flow Methods13. Develop of Flow Reactions September 24, 201214. Flow Chemistry organic-chemistry.org/Highlights/2013/25March.sh tm March 25, 201315. Flow Chemistry organic-chemistry.org/Highlights/2013/30Septembe r.shtm September 30, 2013C-H Functionalization16. C-H Functionalization: The Ono/Kato/Dairi Synthesis of Fusiocca-1,10(14)-diene-3,8?,16-triol organic-chemistry.org/Highlights/2012/19March.sh tm March 19, 201217. C-H Functionalization organic-chemistry.org/Highlights/2012/17Septembe r.shtm September 17, 201218. C-H Functionalization: The Hatakeyama Synthesis of (-)-Kaitocephalin organic-chemistry.org/Highlights/2013/28January. shtm January 28, 201319. C-H Functionalization organic-chemistry.org/Highlights/2013/16Septembe r.shtm September 16, 201320. Natural Product Synthesis by C-H Functionalization: (±)-Allokainic Acid (Wee), (-)-Cameroonan-7?-ol (Taber), (+)-Lithospermic Acid (Yu), (-)-Manabacanine (Kroutil), Streptorubin B and Metacycloprodigiosin (Challis) organic-chemistry.org/Highlights/2012/30January. shtm January 30, 201221. Natural Product Synthesis by C-H Functionalization: (-)-Zampanolide (Ghosh), Muraymycin D2 (Ichikawa), (+)-Sundiversifolide (Iwabuchi), (+)-Przewalskin B (Zhang/Tu), Artemisinin (Wu) organic-chemistry.org/Highlights/2012/11June.sht m June 11, 2012Carbon-Carbon Bond Construction22. Carbon-Carbon Bond Formation: The Bergman Synthesis of (+)-Fuligocandin B organic-chemistry.org/Highlights/2012/12March.sh tm March 12, 201223. C-C Bond Formation: The Petrov Synthesis of Combretastatin A-4 organic-chemistry.org/Highlights/2012/18June.sht m June 18, 201224. Carbon-Carbon Bond Construction: The Baran Synthesis of (+)-Chromazonarol organic-chemistry.org/Highlights/2013/11March.sh tm March 11, 201325. Carbon-Carbon Bond Construction organic-chemistry.org/Highlights/2013/29July.sht m July 29, 201326. Reactions Involving C-C Bond Cleavage organic-chemistry.org/Highlights/2013/23Septembe r.shtm September 23, 2013Reactions of Alkenes27. Reactions of Alkenes: The RajanBabu Synthesis of Pseudopterosin G-J Aglycone Dimethyl Ether March 26, 201228. Reactions of Alkenes organic-chemistry.org/Highlights/2012/10Septembe r.shtm September 10, 201229. Reactions of Alkenes organic-chemistry.org/Highlights/2013/18March.sh tm March 18, 201330. Synthesis and Reactions of Alkenes organic-chemistry.org/Highlights/2013/09Septembe r.shtm September 9, 201331. Advances in Alkene Metathesis: The Kobayashi Synthesis of (+)-TMC-151C organic-chemistry.org/Highlights/2012/23January. shtm January 23, 2012Enantioselective Construction of Acyclic Stereogenic Centers32. Enantioselective Synthesis of Alcohols and Amines: The Ichikawa Synthesis of (+)-Geranyllinaloisocyanide organic-chemistry.org/Highlights/2012/13February .shtm February 13, 201233. Enantioselective Synthesis of Alcohols and Amines: The Fujii/Ohno Synthesis of (+)-Lysergic Acid organic-chemistry.org/Highlights/2012/16July.sht m July 16, 201234. Asymmetric C-Heteroatom Bond Formation organic-chemistry.org/Highlights/2013/11February .shtm February 11, 201335. Construction of Single Stereocenters organic-chemistry.org/Highlights/2013/15July.sht m July 15, 201336. Enantioselective Construction of Alkylated Centers: The Shishido Synthesis of (+)-Helianane organic-chemistry.org/Highlights/2012/20February .shtm February 20, 201237. Enantioselective Synthesis of Alkylated Centers: The Fukuyama Synthesis of (-)-Histrionicotoxin organic-chemistry.org/Highlights/2012/23July.sht m July 23, 201238. Asymmetric C-C Bond Formation organic-chemistry.org/Highlights/2013/18February .shtm February 18, 201339. Arrays of Stereogenic Centers: The Davies Synthesis of Acosamine organic-chemistry.org/Highlights/2012/27February .shtm February 27, 201240. Construction of Alkylated Stereocenters: The Deng Synthesis of (-)-Isoacanthodoral organic-chemistry.org/Highlights/2013/08July.sht m July 8, 201341. Arrays of Stereogenic Centers: The Barker Synthesis of (+)-Galbelgin organic-chemistry.org/Highlights/2012/30July.sht m July 30, 201242. Arrays of Stereogenic Centers: The Carbery Synthesis of Mycestericin G organic-chemistry.org/Highlights/2013/25February .shtm February 25, 201343. Construction of Stereochemical Arrays organic-chemistry.org/Highlights/2013/22July.sht m July 22, 2013Construction of C-O Rings44. Stereoselective C-O Ring Construction: The Keck Synthesis of Bryostatin 1 organic-chemistry.org/Highlights/2012/09January. shtm January 9, 201245. C-O Ring Construction: The Georg Synthesis of Oximidine II organic-chemistry.org/Highlights/2012/09April.sh tm April 9, 201246. C-O Ring Construction: The Reisman Synthesis of (-)-Acetylaranotin organic-chemistry.org/Highlights/2013/14January. shtm January 14, 201347. C-O Ring Formation organic-chemistry.org/Highlights/2013/08April.sh tm April 8, 201348. C-O Ring Construction: (+)-Varitriol (Liu), (+)-Isatisine A (Panek), (+)-Herboxidiene / GEX1A (Ghosh), (-)-Englerin A (Chain), Platensimycin (Lear/Wright) organic-chemistry.org/Highlights/2012/16January. shtm January 16, 201249. C-O Natural Products: (-)-Hybridalactone (Fürstner), (+)- Anthecotulide (Hodgson), (-)-Kumausallene (Tang), (±)-Communiol E (Kobayashi), (-)-Exiguolide (Scheidt), Cyanolide A (Rychnovsky) organic-chemistry.org/Highlights/2012/16April.sh tm April 16, 201250. C-O Ring Containing Natural Products organic-chemistry.org/Highlights/2013/21January. shtm January 21, 201351. Total Synthesis of C-O Ring-Containing Natural Products organic-chemistry.org/Highlights/2013/15April.sh tm April 15, 2013Construction of C-N Rings52. C-N Ring Construction: The Harrity Synthesis of Quinolizidine (-)-217A organic-chemistry.org/Highlights/2012/23April.sh tm April 23, 201253. New Methods for C-N Ring Construction organic-chemistry.org/Highlights/2012/19November .shtm November 19, 201254. C-N Ring Construction: The Fujii/Ohno Synthesis of (-)-Quinocarcin organic-chemistry.org/Highlights/2013/22April.sh tm April 22, 201355. C-N Ring Construction: The Hoye Synthesis of (±)-Leuconolactam organic-chemistry.org/Highlights/2013/18November .shtm November 18, 201356. Alkaloid Synthesis: (-)-?-Kainic Acid (Cohen), Hyacinthacine A2 (Fox), (-)-Agelastatin A (Hamada), (+)-Luciduline (Barbe), (+)-Lunarine (Fan), (-)-Runanine (Herzon) organic-chemistry.org/Highlights/2012/30April.sh tm April 30, 201257. Alkaloid Synthesis: Indolizidine 207A (Shenvi), (-)-Acetylaranotin (Reisman), Flinderole A (May), Isohaouamine B (Trauner), (-)-Strychnine (MacMillan) organic-chemistry.org/Highlights/2012/26November .shtm November 26, 201258. Alkaloid Synthesis: (+)-Deoxoprosopinine (Krishna), Alkaloid (-)-205B (Micalizio), FR901483 (Huang), (+)-Ibophyllidine (Kwon), (-)-Lycoposerramine-S (Fukuyama), (±)-Crinine (Lautens) organic-chemistry.org/Highlights/2013/29April.sh tm April 29, 201359. Alkaloid Synthesis: Lycoposerramine Z (Bonjoch), Esermethole (Shishido), Goniomitine (Zhu), Grandisine (Taylor), Reserpine (Jacobsen) organic-chemistry.org/Highlights/2013/25November .shtm November 25, 2013Substituted Benzene Derivatives60. Substituted Benzenes: The Reddy Synthesis of Isofregenedadiol organic-chemistry.org/Highlights/2012/25June.sht m June 25, 201261. Substituted Benzenes: The Alvarez-Manzaneda Synthesis of (-)-Akaol A organic-chemistry.org/Highlights/2012/08October. shtm October 8, 201262. Substituted Benzenes: The Subba Reddy Synthesis of 7-Desmethoxyfusarentin organic-chemistry.org/Highlights/2013/17June.sht m June 17, 201363. Substituted Benzenes: The Gu Synthesis of Rhazinal organic-chemistry.org/Highlights/2013/14October. shtm October 14, 2013Heteroaromatic Derivatives64. Heteroaromatic Construction: The Sperry Synthesis of (+)-Terreusinone organic-chemistry.org/Highlights/2012/09July.sht m July 9, 201265. Heteroaromatic Construction: The Sato Synthesis of (-)-Herbindole organic-chemistry.org/Highlights/2012/15October. shtm October 15, 201266. Advances in Heterocyclic Aromatic Construction organic-chemistry.org/Highlights/2013/24June.sht m June 24, 201367. Synthesis of Heteroaromatics organic-chemistry.org/Highlights/2013/21October. shtm October 21, 2013Organocatalyzed C-C Ring Construction68. Organocatalytic Carbocyclic Construction: The You Synthesis of (-)-Mesembrine organic-chemistry.org/Highlights/2012/20August.s htm August 20, 201269. Organocatalyzed Carbocyclic Construction: (+)-Roseophilin (Flynn) and (+)-Galbulin (Hong) organic-chemistry.org/Highlights/2012/10December .shtm December 10, 201270. Organocatalytic C-C Ring Construction: Prostaglandin F2? (Aggarwal) organic-chemistry.org/Highlights/2013/12August.s htm August 12, 201371. Organocatalyzed C-C Ring Construction: The Hayashi Synthesis of PGE1 Me Ester organic-chemistry.org/Highlights/2013/16December .shtm December 16, 2013Metal-Mediated C-C Ring Construction72. Metal-Mediated Carbocyclic Construction: The Chen Synthesis of Ageliferin organic-chemistry.org/Highlights/2012/13August.s htm August 13, 201273. Metal-Mediated Carbocyclic Construction: The Whitby Synthesis of (+)-Mucosin organic-chemistry.org/Highlights/2012/17December .shtm December 17, 201274. Metal-Mediated C-C Ring Construction: (+)-Shiromool (Baran) organic-chemistry.org/Highlights/2013/19August.s htm August 19, 201375. Metal-Mediated Ring Construction: The Hoveyda Synthesis of (-)-Nakadomarin A organic-chemistry.org/Highlights/2013/09December .shtm December 9, 2013Intermolecular and Intramolecular Diels-Alder Reactions76. Intramolecular Diels-Alder Cycloaddition: 7-Isocyanoamphilecta-11(20),15-diene (Miyaoka), (-)-Scabronine G (Kanoh), Basiliolide B (Stoltz), Hirsutellone B (Uchiro), Echinopine A (Chen) organic-chemistry.org/Highlights/2012/27August.s htm August 27, 201277. Diels-Alder Cycloaddition: Fawcettimine (Williams), Apiosporic Acid (Helmchen), Marginatone (Abad-Somovilla), Okilactomycin (Hoye), Vinigrol (Barriault), Plakotenin (Bihlmeier/Klopper) organic-chemistry.org/Highlights/2012/24December .shtm December 24, 201278. Diels-Alder Cycloaddition: Defucogilvocarcin V (Bodwell), (+)-Carrisone (Danishefsky), (+)-Fusarisetin A (Theodorakis), 9?-Presilphiperfolan-1?-ol (Stoltz), 7-Isocyano-11(20), 14-epiamphilectadiene (Shenvi) organic-chemistry.org/Highlights/2013/26August.s htm August 26, 201379. Diels-Alder Cycloaddition: (+)-Armillarivin (Banwell), Gelsemiol (Gademann), (+)-Frullanolide (Liao), Myceliothermophin A (Uchiro), Peribysin E (Reddy), Caribenol A (Li/Yang) organic-chemistry.org/Highlights/2013/23December .shtm December 23, 2013Stereocontrolled C-C Ring Construction80. Chloranthalactone (Liu), Rumphellaone A (Kuwahara), Lactiflorin (Bach), Echinosporin (Hale), Harveynone (Taylor), (6,7-deoxy)-Yuanhuapin (Wender) organic-chemistry.org/Highlights/2012/31December .shtm December 31, 201281. Other Methods for C-C Ring Construction: The Liang Synthesis of Echinopine B organic-chemistry.org/Highlights/2013/30December .shtm December 30, 2013Classics in Total Synthesis82. The Reisman Synthesis of (+)-Salvileucalin B organic-chemistry.org/Highlights/2012/02January. shtm January 2, 201283. The Theodorakis Synthesis of (-)-Jiadifenolide organic-chemistry.org/Highlights/2012/06February .shtm February 6, 201284. The Yamashita/Hirama Synthesis of Cortistatin A organic-chemistry.org/Highlights/2012/05March.sh tm March 5, 201285. The Reisman Synthesis of (-)-Maoecrystal Z organic-chemistry.org/Highlights/2012/02April.sh tm April 2, 201286. The Tan/Chen/Yang Synthesis of Schindilactone A organic-chemistry.org/Highlights/2012/07May.shtm May 7, 201287. The Garg Synthesis of (-)-N-Methylwelwitindolinone C organic-chemistry.org/Highlights/2012/04June.sht m June 4, 201288. The Krische Synthesis of Bryostatin 7 organic-chemistry.org/Highlights/2012/02July.sht m July 2, 201289. The Fukuyama Synthesis of Gelsemoxonine organic-chemistry.org/Highlights/2012/06August.s htm August 6, 201290. The Carreira Synthesis of (+)-Daphmanidin E organic-chemistry.org/Highlights/2012/03Septembe r.shtm September 3, 201291. The Qin Synthesis of (+)-Gelsemine organic-chemistry.org/Highlights/2012/01October. shtm October 1, 201292. The Carreira Synthesis of Indoxamycin B organic-chemistry.org/Highlights/2012/05November .shtm November 5, 201293. The Nicolaou/Li Synthesis of Tubingensin A organic-chemistry.org/Highlights/2012/03December .shtm December 3, 201294. The Thomson Synthesis of (-)-GB17 organic-chemistry.org/Highlights/2013/07January. shtm January 7, 201395. The Li Synthesis of (-)-Fusarisetin A organic-chemistry.org/Highlights/2013/04February .shtm February 4, 201396. The Carreira Synthesis of (-)-Dendrobine organic-chemistry.org/Highlights/2013/04March.sh tm March 4, 201397. The Vanderwal Synthesis of Echinopine B organic-chemistry.org/Highlights/2013/01April.sh tm April 1, 201398. The Dixon Synthesis of Manzamine A organic-chemistry.org/Highlights/2013/06May.shtm May 6, 201399. The Williams Synthesis of (-)-Khayasin organic-chemistry.org/Highlights/2013/03June.sht m June 3, 2013100. The Kuwahara Synthesis of Paspalinine organic-chemistry.org/Highlights/2013/01July.sht m July 1, 2013101. The Ma Synthesis of Gracilamine organic-chemistry.org/Highlights/2013/05August.s htm August 5, 2013102. The Carreira Synthesis of (±)-Gelsemoxonine organic-chemistry.org/Highlights/2013/02Septembe r.shtm September 2, 2013103. The Evans Synthesis of (-)-Nakadomarin A organic-chemistry.org/Highlights/2013/07October. shtm October 7, 2013104. The Procter Synthesis of (+)-Pleuromutilin organic-chemistry.org/Highlights/2013/04November .shtm November 4, 2013105. The Harran Synthesis of (+)-Roseophilin organic-chemistry.org/Highlights/2013/02December .shtm December 2, 2013