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Unified total synthesis of pteriatoxins and their diastereomers.

ABSTRACT: A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.

SUBMITTER: Matsuura F

PROVIDER: S-EPMC2515931 | biostudies-literature | 2006 Jun

REPOSITORIES: biostudies-literature

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Unified total synthesis of pteriatoxins and their diastereomers.

Matsuura Fumiyoshi F Peters René R Anada Masahiro M Harried Scott S SS Hao Junliang J Kishi Yoshito Y

Journal of the American Chemical Society 20060601 23

A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process. ...[more]

PMID: 16756299

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