Total Synthesis of (+)‐3‐Deoxyfortalpinoid F, (+)‐Fortalpinoid A, and (+)‐Cephinoid H
Zhiqiang Ren, Zhongliu Sun, Yifei Li, Xin Fan, Mingda Dai, Yunxia Wang, Xiangdong Hu
Abstract
3-Deoxyfortalpinoid F, fortalpinoid A, and cephinoid H are members of the Cephalotaxus diterpenoids class of natural products, which feature diverse chemical structures and valuable biological activities. We report herein the development of a diastereoselective Pauson-Khand reaction as an effective pathway to access the core tetracyclic skeleton, which is found widely in Cephalotaxus diterpenoids. Furthermore, we enabled the construction of the tropone moiety through a ring-closing metathesis/elimination protocol. Based on the developed strategy, asymmetric synthesis of the title compounds has been achieved for the first time.
Topics & Concepts
TroponeMoietyRing-closing metathesisTotal synthesisStereochemistryRing (chemistry)MetathesisChemistrySalt metathesis reactionCombinatorial chemistryOrganic chemistryPolymerizationPolymerBiological Activity of Diterpenoids and BiflavonoidsNatural product bioactivities and synthesisBioactive Natural Diterpenoids Research