Total Syntheses of Uncommon C30 Terpenoids: Chamaecydin and Isochamaecydin

Org Lett. 2023 Nov 3;25(43):7769-7774. doi: 10.1021/acs.orglett.3c02483. Epub 2023 Oct 20.

Abstract

(-)-Chamaecydin and (-)-isochamaecydin, two uncommon C30 terpenoids comprising abietane-type diterpenes and thujane-type monoterpenes, were achieved from β-pinene with (-)-sabinene in 18 and 20 steps, respectively. Key steps include a Claisen-Ireland rearrangement to establish the all-carbon quaternary center, a Rh catalyzed C-H bond insertion reaction to install a spiro-five-membered ring and a Lewis acid promoted cyclization of polyenes to construct the two six-membered rings.