Bioinspired Total Synthesis of (±)-Yezo’otogirin C

The first and protective group-free total synthesis of (±)-yezo’otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (±)-yezo’otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/M...

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Bibliographic Details
Published in:Organic letters 2014-01, Vol.16 (2), p.496-499
Main Authors: He, Shuzhong, Yang, Wei, Zhu, Lizhi, Du, Guangyan, Lee, Chi-Sing
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Cyclohexanones - chemistry
Hypericum - chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
Thiourea - chemistry
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Summary:The first and protective group-free total synthesis of (±)-yezo’otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (±)-yezo’otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403374h