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Total synthesis and stereochemistry of pinnatoxins B and C.

ABSTRACT: [Structure: see text] Pinnatoxins B and C were synthesized from diols (34R)-3b and (34S)-3a, respectively, in a stereochemically controlled manner. Through extensive analysis of the 1H NMR spectra of synthetic PnTXs B and C, the diagnostic NMR signals were first identified to differentiate (34S)- and (34R)-diastereomers and then used to establish the C34 configuration of natural PnTXs B and C as 34S and 34R, respectively.

SUBMITTER: Matsuura F 

PROVIDER: S-EPMC2532836 | biostudies-literature | 2006 Jul

REPOSITORIES: biostudies-literature

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Total synthesis and stereochemistry of pinnatoxins B and C.

Matsuura Fumiyoshi F   Hao Junliang J   Reents Reinhard R   Kishi Yoshito Y  

Organic letters 20060701 15

[Structure: see text] Pinnatoxins B and C were synthesized from diols (34R)-3b and (34S)-3a, respectively, in a stereochemically controlled manner. Through extensive analysis of the 1H NMR spectra of synthetic PnTXs B and C, the diagnostic NMR signals were first identified to differentiate (34S)- and (34R)-diastereomers and then used to establish the C34 configuration of natural PnTXs B and C as 34S and 34R, respectively. ...[more]

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