Synthesis of Tricyclo[4,3,1,01,5]decane Core of Plumisclerin A Using Pauson–Khand Annulation and SmI2-Mediated Radical Cyclization | Zendy

Jipeng Chen | Zendy; Wei He | Zendy; ZhenYu Yang | Zendy; ZhuJun Yao | Zendy

Open Access

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

Author(s) -

Jipeng Chen,

Wei He,

ZhenYu Yang,

ZhuJun Yao

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b01563

Subject(s) - moiety , chemistry , decane , annulation , conjugate , synthon , stereochemistry , core (optical fiber) , molecule , organic chemistry , catalysis , mathematical analysis , mathematics , materials science , composite material

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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