Total Synthesis of (±)-Kopsihainanine A

Going all the way: The first total synthesis of (±)‐kopsihainanine A has been achieved in ten steps with a 12 % overall yield from commercially available 1,2,3,4‐tetrahydrocarbazol‐4‐one (see scheme). This synthesis features an intramolecular conjugate addition of the iminium ion formed in situ with...

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Bibliographic Details
Published inChemistry : a European journal Vol. 18; no. 22; pp. 6729 - 6732
Main Authors Jing, Peng, Yang, Zhen, Zhao, Changgui, Zheng, Huaiji, Fang, Bowen, Xie, Xingang, She, Xuegong
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 29.05.2012
WILEY‐VCH Verlag
Wiley
Subjects
alkaloids
Chemistry
Chemistry, Multidisciplinary
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
indoles
intramolecular conjugate addition
kopsihainanine A
Molecular Structure
oxidation
Oxidation-Reduction
Physical Sciences
Science & Technology
Stereoisomerism
total synthesis
kopsihainanine A
ENANTIOSELECTIVE SYNTHESIS
alkaloids
oxidation
QUATERNARY CARBON CENTERS
INTRAMOLECULAR RITTER REACTION
indoles
total synthesis
INDOLE ALKALOIDS
CORE STRUCTURE
AMINOCYCLOPROPANES
intramolecular conjugate addition
CYCLIZATION
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Summary:Going all the way: The first total synthesis of (±)‐kopsihainanine A has been achieved in ten steps with a 12 % overall yield from commercially available 1,2,3,4‐tetrahydrocarbazol‐4‐one (see scheme). This synthesis features an intramolecular conjugate addition of the iminium ion formed in situ with the amide and a substrate‐controlled diastereoselective α‐hydroxylation. Furthermore, ring D is formed by a late‐stage transannular SN2 reaction.
Bibliography:ark:/67375/WNG-B18RKD70-G
MOST - No. 2010CB833200
NSFC - No. 21125207; No. 21072086; No. 21102062
istex:B7912C680EAF43828CF86A533E92E19837C30848
ArticleID:CHEM201200867
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0947-6539
1521-3765
1521-3765
DOI:10.1002/chem.201200867