223575-40-4Relevant academic research and scientific papers
Radical-mediated construction of cyclopentane with concurrent formation of a well-defined quaternary center
Zhu,Qiao,Wu,Wu
, p. 2428 - 2432 (1999)
Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.
