4.5 Article

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

Journal

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 15, Issue -, Pages 858-862

Publisher

BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.15.83

Keywords

domino reactions; metathesis; Michael addition; organocatalysis; terpenes

Funding

  1. Alexander von Humboldt Foundation

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(-)-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.

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