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Total Synthesis of Limaol.

ABSTRACT: A nonthermodynamic array of four skipped methylene substituents on the hydrophobic tail renders limaol, a C40-polyketide of marine origin, unique in structural terms. This conspicuous segment was assembled by a two-directional approach and finally coupled to the polyether domain by an allyl/alkenyl Stille reaction under neutral conditions. The core region itself was prepared via a 3,3'-dibromo-BINOL-catalyzed asymmetric propargylation, a gold-catalyzed spirocyclization, and introduction of the southern sector via substrate-controlled allylation as the key steps.

SUBMITTER: Hess SN

PROVIDER: S-EPMC7888267 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Total Synthesis of Limaol.

Hess Stephan N SN Mo Xiaobin X Wirtz Conny C Fürstner Alois A

Journal of the American Chemical Society 20210203 6

A nonthermodynamic array of four skipped methylene substituents on the hydrophobic tail renders limaol, a C40-polyketide of marine origin, unique in structural terms. This conspicuous segment was assembled by a two-directional approach and finally coupled to the polyether domain by an allyl/alkenyl Stille reaction under neutral conditions. The core region itself was prepared via a 3,3'-dibromo-BINOL-catalyzed asymmetric propargylation, a gold-catalyzed spirocyclization, and introduction of the s ...[more]

PMID: 33533589

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