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

Ji-Peng Chen, Wei He, Zhen-Yu Yang, Zhu-Jun Yao

Organic letters 2015 Jul 17

filter terms:

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.

Citation

Ji-Peng Chen, Wei He, Zhen-Yu Yang, Zhu-Jun Yao. Synthesis of Tricyclo[4,3,1,0(1,5)]decane Core of Plumisclerin A Using Pauson-Khand Annulation and SmI2-Mediated Radical Cyclization. Organic letters. 2015 Jul 17;17(14):3379-81