Bufadienolides. 11. Bufalin and resibufogenin

George Pettit; Leonard E. Houghton; John C. Knight; Fred Bruschweiler

doi:10.1021/jo00834a008

Bufadienolides. 11. Bufalin and resibufogenin

George Pettit, Leonard E. Houghton, John C. Knight, Fred Bruschweiler

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Abstract

A total synthesis of resibufogenin (12b) and bufalin (1a) has been summarized. Digitoxigenin (2a) was employed as relay and converted to 14-dehydrobufalin acetate (11). The latter substance was transformed to resibufogenin (12b) and bufalin (1a). The synthesis represents a new approach to the bufadienolides and constitutes the first synthetic route from a cardenolide to a bufadienolide.

Original language	English (US)
Pages (from-to)	2895-2898
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	35
Issue number	9
DOIs	https://doi.org/10.1021/jo00834a008
State	Published - Jan 1 1970

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Organic Chemistry

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AU - Knight, John C.

AU - Bruschweiler, Fred

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Y1 - 1970/1/1

N2 - A total synthesis of resibufogenin (12b) and bufalin (1a) has been summarized. Digitoxigenin (2a) was employed as relay and converted to 14-dehydrobufalin acetate (11). The latter substance was transformed to resibufogenin (12b) and bufalin (1a). The synthesis represents a new approach to the bufadienolides and constitutes the first synthetic route from a cardenolide to a bufadienolide.

AB - A total synthesis of resibufogenin (12b) and bufalin (1a) has been summarized. Digitoxigenin (2a) was employed as relay and converted to 14-dehydrobufalin acetate (11). The latter substance was transformed to resibufogenin (12b) and bufalin (1a). The synthesis represents a new approach to the bufadienolides and constitutes the first synthetic route from a cardenolide to a bufadienolide.

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Bufadienolides. 11. Bufalin and resibufogenin

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