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Stereoselective total synthesis of (+/-)-tochuinyl acetate and (+/-)-dihydrotochuinyl acetates

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Publisher
Elsevier Science
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Keywords
  • Organic Chemistry

Abstract

Details of the first total synthesis of the marine natural product dihydrotochuinyl acetate is described. Cyclopentenone annulation of p-methylacetophenone via a Claisen rearrangement-Wacker oxidation based sequence generated the cyclopentenone 3, a known precursor for the sesquiterpenes cuparene, laurene, alpha-cuparenone and beta-cuparenones. Conversion of the ketone moiety into a carboxylate followed by stereoselective alkylation and reduction transformed the cyclopentenone 3 into the primary alcohol 19. Birch reduction of the alcohol 19 followed by acetylation furnished (+/-)-dihydrotochuinyl acetate, whereas direct acetylation of 19 furnished (+/-)-tochuinyl acetate. (C) 1998 Elsevier Science Ltd. All rights reserved.

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