Abstract 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 ...
[Clark, Brady K.; Culshaw, Peter N.; Griller, David; Lossing, F. P.; Simoes, J. A. Martinho; Walton, John C. Journal of Organic Chemistry, 1991 , vol. 56, # 19 p. 5535 - 5539]