Synthesis of Tricyclo[4,3,1,0(1,5)]decane Core of Plumisclerin A Using Pauson-Khand Annulation and SmI2-Mediated Radical Cyclization.

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Abstract

An efficient synthesis of the tricyclo[4,3,1,0(1, 5)]decane core (B/C/D rings) of plumisclerin A, a unique cytotoxic marine diterpenoid, is described. A Pauson-Khand reaction and a SmI2-mediated radical 1,4-conjugate addition successfully served as key reactions for construction of the fully functionalized 5,6-fused rings and the highly strained cyclobutanol moiety with correct relative stereochemistries, respectively.

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Journal

Journal ID (iso-abbrev): Org. Lett.

Title: Organic letters

Publisher: American Chemical Society (ACS)

ISSN (Electronic): 1523-7052

ISSN (Print): 1523-7052

Publication date (Electronic): Jul 17 2015

Volume: 17

Issue: 14

Affiliations

[1 ] State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Article

DOI: 10.1021/acs.orglett.5b01563

PubMed ID: 26118407

SO-VID: dbf5342a-d484-4981-8fc8-f30080f7cbab

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