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Highly convergent total synthesis of (+)-lithospermic acid via a late-stage intermolecular C-H olefination.

ABSTRACT: The total synthesis of (+)-lithospermic acid is reported, which exploits two successive C-H activation reactions as key steps. Rh-catalyzed carbene C-H insertion reaction utilizing Davies's catalyst was used to forge dihydrobenzofuran core, and a late-stage intermolecular C-H olefination coupled the olefin unit with the dihydrobenzofuran core to construct the molecule in a highly convergent manner.

SUBMITTER: Wang DH

PROVIDER: S-EPMC3085405 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Highly convergent total synthesis of (+)-lithospermic acid via a late-stage intermolecular C-H olefination.

Wang Dong-Hui DH Yu Jin-Quan JQ

Journal of the American Chemical Society 20110328 15

The total synthesis of (+)-lithospermic acid is reported, which exploits two successive C-H activation reactions as key steps. Rh-catalyzed carbene C-H insertion reaction utilizing Davies's catalyst was used to forge dihydrobenzofuran core, and a late-stage intermolecular C-H olefination coupled the olefin unit with the dihydrobenzofuran core to construct the molecule in a highly convergent manner. ...[more]

PMID: 21443224

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