Steroids and related natural products-X. Reduction of lactones

G. R. Pettit, B. Green, T. R. Kasturi, U. R. Ghatak

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

Boron trifluoride etherate-lithium aluminum hydride reduction of 12β-hydroxy-14ξ-rosane 16-carboxylic acid lactone (IIa), dihydroabietic γ-lactone (IIIa) and 3β-hydroxy-7-oxo-7a-oxa-B- homo-5α-cholestane (Xa) was found to yield the corresponding (IIb and IIIb) and oxepane (Xb, after acetylation) derivatives. Similar reduction of several lactones prepared from primary alcohols resulted in essentially complete conversion to their respective glycols. For example, only 3,4-dihydroxy-3,4-seco-5α-androstane (IX) was isolated following reduction of 3-oxo-3a-oxa-A-homo- 5α-androstane (VII). The present study suggests that boron trifluoride-lithium aluminum hydride reduction of esters will increasingly favor ether formation as branching adjacent to the ester alkyl-oxygen moiety increases.

Original languageEnglish (US)
Pages (from-to)953-958
Number of pages6
JournalTetrahedron
Volume18
Issue number8
DOIs
StatePublished - 1962
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Steroids and related natural products-X. Reduction of lactones'. Together they form a unique fingerprint.

  • Cite this