Steroids and related natural products-X. Reduction of lactones

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

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
StatePublished - 1962
Externally publishedYes

Fingerprint

Lactones
Biological Products
Steroids
Esters
Cholestanes
Glycols
Acetylation
Carboxylic Acids
Ether
Alcohols
Oxygen
Derivatives
lithium aluminum hydride
androstane

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Biochemistry

Cite this

Pettit, G., Green, B., Kasturi, T. R., & Ghatak, U. R. (1962). Steroids and related natural products-X. Reduction of lactones. Tetrahedron, 18(8), 953-958.

Steroids and related natural products-X. Reduction of lactones. / Pettit, George; Green, B.; Kasturi, T. R.; Ghatak, U. R.

In: Tetrahedron, Vol. 18, No. 8, 1962, p. 953-958.

Research output: Contribution to journalArticle

Pettit, G, Green, B, Kasturi, TR & Ghatak, UR 1962, 'Steroids and related natural products-X. Reduction of lactones', Tetrahedron, vol. 18, no. 8, pp. 953-958.
Pettit G, Green B, Kasturi TR, Ghatak UR. Steroids and related natural products-X. Reduction of lactones. Tetrahedron. 1962;18(8):953-958.
Pettit, George ; Green, B. ; Kasturi, T. R. ; Ghatak, U. R. / Steroids and related natural products-X. Reduction of lactones. In: Tetrahedron. 1962 ; Vol. 18, No. 8. pp. 953-958.
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