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Enantioselective Syntheses of (-)-Alloyohimbane and (-)-Yohimbane by an Efficient Enzymatic Desymmetrization Process.

ABSTRACT: Enantioselective syntheses of (-)-alloyohimbane and (-)-yohimbane was accomplished in a convergent manner. The key step involved a modified mild protocol for the enantioselective enzymatic desymmetrization of meso-diacetate. The protocol provided convenient access to an optically active monoacetate in multi-gram scale in high enantiomeric purity. This monoacetate was converted to (-)-alloyohimbane. Reductive amination of the derived aldehyde causes the isomerization leading to the trans-product and allows the synthesis of (-)-yohimbane.

SUBMITTER: Ghosh AK

PROVIDER: S-EPMC5526648 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Enantioselective Syntheses of (-)-Alloyohimbane and (-)-Yohimbane by an Efficient Enzymatic Desymmetrization Process.

Ghosh Arun K AK Sarkar Anindya A

European journal of organic chemistry 20161128 36

Enantioselective syntheses of (-)-alloyohimbane and (-)-yohimbane was accomplished in a convergent manner. The key step involved a modified mild protocol for the enantioselective enzymatic desymmetrization of <i>meso</i>-diacetate. The protocol provided convenient access to an optically active monoacetate in multi-gram scale in high enantiomeric purity. This monoacetate was converted to (-)-alloyohimbane. Reductive amination of the derived aldehyde causes the isomerization leading to the <i>tran ...[more]

PMID: 28757804

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