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An efficient synthesis of the guaiane sesquiterpene (-)-isoguaiene by domino metathesis.

ABSTRACT: (-)-Isoguaiene was prepared from (S)-citronellal in only 9-10 steps with good overall yields. Either a trienyne or a dienediyne metathesis and highly diastereoselective organocatalytic Michael additions of aldehydes derived from (S)-citronellal served as the key transformations.

SUBMITTER: Wang Y 

PROVIDER: S-EPMC6466796 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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An efficient synthesis of the guaiane sesquiterpene (-)-isoguaiene by domino metathesis.

Wang Yuzhou Y   Darweesh Ahmed F AF   Zimdars Patrick P   Metz Peter P  

Beilstein journal of organic chemistry 20190409

(-)-Isoguaiene was prepared from (<i>S</i>)-citronellal in only 9-10 steps with good overall yields. Either a trienyne or a dienediyne metathesis and highly diastereoselective organocatalytic Michael additions of aldehydes derived from (<i>S</i>)-citronellal served as the key transformations. ...[more]

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