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Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin.

ABSTRACT: The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin have been accomplished. These syntheses were based on a common parallel synthetic strategy using Prins-Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle with the correct cis-stereochemistry ring closure and the Δ⁴ position of the endocyclic double bond in (+)-isolaurepinnacin was obtained. This unsaturation was also necessary to accede to the bromodioxabicycle on (+)-neoisoprelaurefucin.

SUBMITTER: Sinka V

PROVIDER: S-EPMC9344465 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin.

Sinka Victoria V Cruz Daniel A DA Martín Víctor S VS Padrón Juan I JI

Organic letters 20220714 29

The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin have been accomplished. These syntheses were based on a common parallel synthetic strategy using Prins-Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle with the correct <i>cis</i>-stereochemistry ring closure and the Δ<sup>4</sup> position of the endocyclic double bond in (+)-isolaurepinnacin was obtained. This unsaturation was also necessary to acced ...[more]

PMID: 35834432

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