Steroids and Related Natural Products. 88. Synthesis of Periplogenin

Yoshiaki Kamano; George Pettit; M. Tozawa

doi:10.1021/jo00929a054

Steroids and Related Natural Products. 88. Synthesis of Periplogenin

Yoshiaki Kamano, George Pettit, M. Tozawa

Research output: Contribution to journal › Letter › peer-review

Abstract

Digitoxigenin (3a) was converted to canarigenin (6), periplogenin (1c), and uzarigenin (3b); the use of tert-butyl hypochlorite for oxidation of digitoxigenin (3a) to chloro ketone 4 and application of chromium(II) acetate for reduction of epoxy ketone 7 to hydroxy ketone 8 represented particularly convenient aspects of these synthetic transformations.

Original language	English (US)
Pages (from-to)	2319-2320
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	39
Issue number	15
DOIs	https://doi.org/10.1021/jo00929a054
State	Published - Jul 1 1974

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00929a054

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abstract = "Digitoxigenin (3a) was converted to canarigenin (6), periplogenin (1c), and uzarigenin (3b); the use of tert-butyl hypochlorite for oxidation of digitoxigenin (3a) to chloro ketone 4 and application of chromium(II) acetate for reduction of epoxy ketone 7 to hydroxy ketone 8 represented particularly convenient aspects of these synthetic transformations.",

author = "Yoshiaki Kamano and George Pettit and M. Tozawa",

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AU - Pettit, George

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N2 - Digitoxigenin (3a) was converted to canarigenin (6), periplogenin (1c), and uzarigenin (3b); the use of tert-butyl hypochlorite for oxidation of digitoxigenin (3a) to chloro ketone 4 and application of chromium(II) acetate for reduction of epoxy ketone 7 to hydroxy ketone 8 represented particularly convenient aspects of these synthetic transformations.

AB - Digitoxigenin (3a) was converted to canarigenin (6), periplogenin (1c), and uzarigenin (3b); the use of tert-butyl hypochlorite for oxidation of digitoxigenin (3a) to chloro ketone 4 and application of chromium(II) acetate for reduction of epoxy ketone 7 to hydroxy ketone 8 represented particularly convenient aspects of these synthetic transformations.

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Steroids and Related Natural Products. 88. Synthesis of Periplogenin

Abstract

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