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Russian Chemical Bulletin

, Volume 47, Issue 6, pp 1162–1165 | Cite as

A short synthesis of diastereomeric norambraketals

  • I. Yu. Andreeva
  • A. N. Aryku
  • P. F. Vlad
Organic Chemistry

Abstract

A short synthesis of diastereomeric norambraketals was accomplished starting from norambreinolide. The reaction of norambreinolide with methyllithium followed by dehydration of the obtained 8α-hydroxy-14,15,16-trinorlabdan-12-one gave 14,15,16-trinorlabd-8(17)-en-12-one. Oxidation of the latter with OsO4 or peracids with subsequent isomerization of the formed epoxy ketone leads, respectively, to (12R)-8α,12∶12,17- and (12S)-8β,12∶12,17-diepoxy-14,15,16-trinorlabdans. Only the former is fragrant and possesses ambergris odor.

Key words

norambraketals norambreinolide 14,15,16-trinorlabd-8(17)-en-12-one synthesis oxidation ambergris odor 

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Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • I. Yu. Andreeva
    • 1
  • A. N. Aryku
    • 1
  • P. F. Vlad
    • 1
  1. 1.Institute of ChemistryAcademy of Sciences of Republic of MoldovaKishinevRepublic of Moldova

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