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Torsional steering controls the stereoselectivity of epoxidation in the guanacastepene a synthesis.

ABSTRACT: [reaction: see text] The stereoselectivity of the key epoxidation step in the synthesis of guanacastepene A is shown to be controlled by torsional steering. In this particular epoxidation reaction, the transition structure energetic difference is enhanced by the great asynchronicity of the forming C-O bonds that intensifies the torsional interactions.

SUBMITTER: Cheong PH

PROVIDER: S-EPMC3164362 | biostudies-literature | 2006 Apr

REPOSITORIES: biostudies-literature

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Torsional steering controls the stereoselectivity of epoxidation in the guanacastepene a synthesis.

Cheong Paul Ha-Yeon PH Yun Heedong H Danishefsky Samuel J SJ Houk K N KN

Organic letters 20060401 8

[reaction: see text] The stereoselectivity of the key epoxidation step in the synthesis of guanacastepene A is shown to be controlled by torsional steering. In this particular epoxidation reaction, the transition structure energetic difference is enhanced by the great asynchronicity of the forming C-O bonds that intensifies the torsional interactions. ...[more]

PMID: 16597098

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