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An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B.

ABSTRACT: This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.

SUBMITTER: Kong K

PROVIDER: S-EPMC6775640 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B.

Kong Ke K Enquist John A JA McCallum Monica E ME Smith Genessa M GM Matsumaru Takanori T Menhaji-Klotz Elnaz E Wood John L JL

Journal of the American Chemical Society 20130718 30

This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step. ...[more]

PMID: 23837485

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