Steroids and Related Natural Products. 69. Synthesis of 20(22)-Dihydro-23-deoxodigitoxigenin

F. Warren Villaescusa; George Pettit

doi:10.1021/jo00969a010

Steroids and Related Natural Products. 69. Synthesis of 20(22)-Dihydro-23-deoxodigitoxigenin

F. Warren Villaescusa, George Pettit

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Abstract

A synthetic route from digitoxigenin to 20(22)-Vdihydro-23-deoxodigitoxigenin (10a) has been developed. Digi-toxigenin was acetylated, dehydrated, and selectively hydrogenated to give 3β-acetoxy-5β;20-card-14-enolide (4). Reduction with lithium aluminum hydride gave diol 5 which was cyclized to yield 3β-hydroxy-23-deoxo-5β,20-card-14-enolide (6). Introduction of the 14β-hydroxyl (10a) group was achieved by successive formation of the 14β-hydroxy-15α-bromo (7) and β-epoxide (8) derivatives followed by a reduction step.

Original language	English (US)
Pages (from-to)	569-572
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	37
Issue number	4
DOIs	https://doi.org/10.1021/jo00969a010
State	Published - Feb 1 1972

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Organic Chemistry

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title = "Steroids and Related Natural Products. 69. Synthesis of 20(22)-Dihydro-23-deoxodigitoxigenin",

abstract = "A synthetic route from digitoxigenin to 20(22)-Vdihydro-23-deoxodigitoxigenin (10a) has been developed. Digi-toxigenin was acetylated, dehydrated, and selectively hydrogenated to give 3β-acetoxy-5β;20-card-14-enolide (4). Reduction with lithium aluminum hydride gave diol 5 which was cyclized to yield 3β-hydroxy-23-deoxo-5β,20-card-14-enolide (6). Introduction of the 14β-hydroxyl (10a) group was achieved by successive formation of the 14β-hydroxy-15α-bromo (7) and β-epoxide (8) derivatives followed by a reduction step.",

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AU - Pettit, George

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N2 - A synthetic route from digitoxigenin to 20(22)-Vdihydro-23-deoxodigitoxigenin (10a) has been developed. Digi-toxigenin was acetylated, dehydrated, and selectively hydrogenated to give 3β-acetoxy-5β;20-card-14-enolide (4). Reduction with lithium aluminum hydride gave diol 5 which was cyclized to yield 3β-hydroxy-23-deoxo-5β,20-card-14-enolide (6). Introduction of the 14β-hydroxyl (10a) group was achieved by successive formation of the 14β-hydroxy-15α-bromo (7) and β-epoxide (8) derivatives followed by a reduction step.

AB - A synthetic route from digitoxigenin to 20(22)-Vdihydro-23-deoxodigitoxigenin (10a) has been developed. Digi-toxigenin was acetylated, dehydrated, and selectively hydrogenated to give 3β-acetoxy-5β;20-card-14-enolide (4). Reduction with lithium aluminum hydride gave diol 5 which was cyclized to yield 3β-hydroxy-23-deoxo-5β,20-card-14-enolide (6). Introduction of the 14β-hydroxyl (10a) group was achieved by successive formation of the 14β-hydroxy-15α-bromo (7) and β-epoxide (8) derivatives followed by a reduction step.

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Steroids and Related Natural Products. 69. Synthesis of 20(22)-Dihydro-23-deoxodigitoxigenin

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