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Selective synthesis of either enantiomer of an anti-breast cancer agent via a common enantioenriched intermediate.

ABSTRACT: A stereoselective synthesis of a bioactive triarylmethane is described. Key to the synthesis is a nickel-catalyzed Suzuki-Miyaura coupling which proceeds with retention at the benzylic center. This method is complementary to our previously reported nickel-catalyzed Kumada coupling which proceeds with inversion. Together, the two methods allow for efficient access to either enantiomer of biologically relevant triarylmethanes from a common enantioenriched intermediate.

SUBMITTER: Johnson AG

PROVIDER: S-EPMC4465125 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Selective synthesis of either enantiomer of an anti-breast cancer agent via a common enantioenriched intermediate.

Johnson Aaron George AG Tranquilli Marissa M MM Harris Michael R MR Jarvo Elizabeth R ER

Tetrahedron letters 20150601 23

A stereoselective synthesis of a bioactive triarylmethane is described. Key to the synthesis is a nickel-catalyzed Suzuki-Miyaura coupling which proceeds with retention at the benzylic center. This method is complementary to our previously reported nickel-catalyzed Kumada coupling which proceeds with inversion. Together, the two methods allow for efficient access to either enantiomer of biologically relevant triarylmethanes from a common enantioenriched intermediate. ...[more]

PMID: 26085695

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