The Catalytic Asymmetric Total Synthesis of Elatol

The Catalytic Asymmetric Total Synthesis of Elatol

Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-clo...

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Veröffentlicht in:Journal of the American Chemical Society 2008-01, Vol.130 (3), p.810-811
Hauptverfasser: White, David E, Stewart, Ian C, Grubbs, Robert H, Stoltz, Brian M
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Sprache:eng
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Catalysis
Sesquiterpenes - chemistry
Spiro Compounds - chemical synthesis
Stereoisomerism
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container_title Journal of the American Chemical Society
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creator White, David E
Stewart, Ian C
Grubbs, Robert H
Stoltz, Brian M
description Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-closing olefin metathesis to concomitantly form the spirocyclic core as well as the fully substituted chlorinated olefin. This strategy represents a general platform for accessing the chamigrene natural product family, as demonstrated by the synthesis of (+)-laurencenone B as an intermediate in our route.
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subjects Catalysis
Sesquiterpenes - chemistry
Spiro Compounds - chemical synthesis
Stereoisomerism
title The Catalytic Asymmetric Total Synthesis of Elatol
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