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Cryptocaryols A and B: total syntheses, stereochemical revision, structure elucidation, and structure-activity relationship.

ABSTRACT: The first total syntheses and structural elucidation of cryptocaryol A and cryptocaryol B were achieved in 23 and 25 linear steps, respectively. The synthesis relied on the use of a key pseudo-Cs symmetric pentaol intermediate, which in a stereochemically divergent manner was converted into either enantiomer as well as diastereomers. This synthetic effort enabled the first structure-activity relationships of this class of PDCD4 stabilizing natural products.

SUBMITTER: Wang Y

PROVIDER: S-EPMC3772640 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Cryptocaryols A and B: total syntheses, stereochemical revision, structure elucidation, and structure-activity relationship.

Wang Yanping Y O'Doherty George A GA

Journal of the American Chemical Society 20130614 25

The first total syntheses and structural elucidation of cryptocaryol A and cryptocaryol B were achieved in 23 and 25 linear steps, respectively. The synthesis relied on the use of a key pseudo-Cs symmetric pentaol intermediate, which in a stereochemically divergent manner was converted into either enantiomer as well as diastereomers. This synthetic effort enabled the first structure-activity relationships of this class of PDCD4 stabilizing natural products. ...[more]

PMID: 23750754

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