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A diastereodivergent synthetic strategy for the syntheses of communesin F and perophoramidine.

ABSTRACT: An efficient, unified, and stereodivergent approach toward communesin F and perophoramidine was examined. The C(3) all-carbon quaternary center of an oxindole was smoothly constructed by base-promoted indolone-malonate alkylation chemistry. The complementary relative stereochemistry of the crucial vicinal quaternary centers found in communesin F and perophoramidine was selectively installed by substrate-controlled decarboxylative allylic alkylations.

SUBMITTER: Han SJ

PROVIDER: S-EPMC4068777 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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A diastereodivergent synthetic strategy for the syntheses of communesin F and perophoramidine.

Han Seo-Jung SJ Vogt Florian F Krishnan Shyam S May Jeremy A JA Gatti Michele M Virgil Scott C SC Stoltz Brian M BM

Organic letters 20140609 12

An efficient, unified, and stereodivergent approach toward communesin F and perophoramidine was examined. The C(3) all-carbon quaternary center of an oxindole was smoothly constructed by base-promoted indolone-malonate alkylation chemistry. The complementary relative stereochemistry of the crucial vicinal quaternary centers found in communesin F and perophoramidine was selectively installed by substrate-controlled decarboxylative allylic alkylations. ...[more]

PMID: 24909760

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