Total Synthesis of (+)-Antroquinonol and (+)-Antroquinonol D

The first total synthesis of (+)-antroquinonol and (+)-antroquinonol D, two structurally unique quinonols with a sesquiterpene side chain, is described. The route features an iridium-catalyzed olefin isomerization–Claisen rearrangement reaction (ICR), lactonization, and Grubbs olefin metathesis. The...

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Bibliographic Details
Published in:Organic letters 2015-03, Vol.17 (5), p.1138-1141
Main Authors: Sulake, Rohidas S, Chen, Chinpiao
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Alkenes - chemistry
Antrodia - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Iridium - chemistry
Molecular Structure
Oxidation-Reduction
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
Ubiquinone - analogs & derivatives
Ubiquinone - chemical synthesis
Ubiquinone - chemistry
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Summary:The first total synthesis of (+)-antroquinonol and (+)-antroquinonol D, two structurally unique quinonols with a sesquiterpene side chain, is described. The route features an iridium-catalyzed olefin isomerization–Claisen rearrangement reaction (ICR), lactonization, and Grubbs olefin metathesis. The requisite α,β-unsaturation was achieved via the selenylation/oxidation protocol and elimination of β-methoxy group to provide two natural products from a common intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00046