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Steroids and related natural products. VIII. Synthesis of oxasteroids

Pettit, GR and Kasturi, TR (1961) Steroids and related natural products. VIII. Synthesis of oxasteroids. In: Journal of Organic Chemistry, 26 (11). pp. 4557-4563.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo01069a087

Abstract

Peroxydisulfuric acid oxidation of testosterone propionate, progesterone, and cholest-4-en-3-one has been shown to yield 3-oxo-17β-hydroxy-4-oxa-5α-androstane (I, after saponification), 3,20-dioxo-4-oxa-5α-pregnane (V) and 3-oxo-4-oxa-5α-cholestane (VII) respectively. Boron trifluoride etherate-lithium aluminum hydride reduction of δ-lactones I, V, and VII led to the corresponding tetrahydropyran derivatives (IIb, VIa, and VIII). Similar reduction of 3β-hydroxy-17-oxo-17a-oxa-D-homo-5α-androstane (XI) gave 3β-hydroxy-17a-oxa-D-homo-5α-androstane (XIIa). Diborane-boron trifluoride etherate was also found to reduce lactones to cyclic ethers, while reduction with diborane gave hemiacetals. Evidence in support of the structures and stereochemistry assigned to the lactones and their unusual reduction products has been summarized. A tentative mechanism is proposed for lactone → ether reduction employing diborane-boron trifluoride etherate.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Others
Date Deposited: 15 Jun 2010 11:26
Last Modified: 19 Sep 2010 06:09
URI: http://eprints.iisc.ernet.in/id/eprint/28420

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