אסיף מאגר המחקר החקלאי

1-oxo-steroids. Part 2. Model studies for the synthesis of the withanolides

Year:

1977

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Weissenberg, M., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel
Lavie, D., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel
Glotter, E., Faculty of Agriculture, Hebrew University of Jerusalem, Rehovot, Israel

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Abstract:

Several cholestane derivatives possessing rings A and B with the same substitution pattern as in the naturally occurring steroidal lactones of the withanolide group have been synthesised: 4β-hydroxycholesta-2,5-dien-1-one (10), 5,6β-epoxy-4β-hydroxy-5β-cholest-2-en-1-one (12), cholesta-2,5-dien-1-one (19), and 5,6β-epoxy-5β-cholest-2-en-1-one (21). Several other compounds in which rings A and B have a substitution pattern not yet encountered among the natural withanolides have also been prepared: 5,6α-epoxy-4β-hydroxy-5α-cholest-2-en-1-one (11), 5,6α-epoxy-5α-cholest-2-en-1-one (20), and 4α-acetoxy-5- hydroxy-5β-cholest-2-en-1-one (28).

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