Total Synthesis of (±)-Przewalskin B

A concise total synthesis of przewalskin B was accomplished from readily available diene 7. Key features of the synthesis involved a Diels–Alder reaction to install the A ring, a Claisen–Johnson rearrangement to establish the spiro-quaternary center, and a ring-closing metathesis (RCM) of a sterical...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-03, Vol.79 (6), p.2746-2750
Main Authors: Xiao, Mingxing, Wei, Lin, Li, Liqi, Xie, Zhixiang
Format: Article
Language:English
Subjects:
Cyclization
Cycloaddition Reaction
Diterpenes - chemical synthesis
Diterpenes - chemistry
Stereoisomerism
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Summary:A concise total synthesis of przewalskin B was accomplished from readily available diene 7. Key features of the synthesis involved a Diels–Alder reaction to install the A ring, a Claisen–Johnson rearrangement to establish the spiro-quaternary center, and a ring-closing metathesis (RCM) of a sterically crowded system to construct the cyclic enone moiety.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500047q