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Diastereoselective Ring Homologation of Bicyclic Hydrazines: Access to cis-1,3-Diaminocyclohexitols.

ABSTRACT: A sequence of oxidative cleavage/double nitroaldol condensation followed by a few simple synthetic transformations can lead to polyhydroxylated di- and triaminocyclohexanes from a readily available bicyclic hydrazine. This new synthetic route provides a simple and general access to densely substituted privileged scaffolds or fragments with a perfect control of their relative configuration.

SUBMITTER: Blond A

PROVIDER: S-EPMC6643457 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Diastereoselective Ring Homologation of Bicyclic Hydrazines: Access to <i>cis</i>-1,3-Diaminocyclohexitols.

Blond Aurélie A Turcaud Serge S Lecourt Thomas T Micouin Laurent L

ACS omega 20181112 11

A sequence of oxidative cleavage/double nitroaldol condensation followed by a few simple synthetic transformations can lead to polyhydroxylated di- and triaminocyclohexanes from a readily available bicyclic hydrazine. This new synthetic route provides a simple and general access to densely substituted privileged scaffolds or fragments with a perfect control of their relative configuration. ...[more]

PMID: 31458191

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