652131-29-8Relevant academic research and scientific papers
Studies towards Simalikalactone D and Quassimarin: Construction of an Advanced Pentacyclic Intermediate
Shing, Tony K. M.,Zhu, Xue Y.,Yeung, Yeung Y.
, p. 5489 - 5500 (2007/10/03)
An advanced pentacyclic intermediate, amenable to further elaboration into the target molecules simalikalactone D and quassimarin, has been synthesized from (S)-(+)-carvone in 21 steps and with an overall yield of 12%. The synthesis is efficient, stereocontrolled, enantiospecific, and chirality productive, creating eight new chiral centres in pentacycle, and should provide opportunities for rapid access to simalikalactone D analogues and other bioactive quassinoids. The reaction sequence involves a regioselective bishydroxylmethylation, a stereocontrolled epoxidation, an epoxymethano-bridge formation, a 1,3-sigmatropic rearrangement and an intramolecular Diels-Alder reaction as the key steps.
