Enyne versus diene RCM in the synthesis of cyclopentene derivatives toward the A ring of FR182877

Jacques-Alexis Funel (1) , Joëlle Prunet (1)

1 DCSO - Laboratoire de synthèse organique

The A ring of FR182877, exemplified by ent-4-b,c, has been synthesized, involving an enyne RCM as the key step. A systematic comparison of enyne vs diene RCM for the formation of cyclopentene derivatives showed that the latter metathesis proceeds much more easily even for this ring size.

Domaines: Chimie organique

Jacques-Alexis Funel, Joëlle Prunet. Enyne versus diene RCM in the synthesis of cyclopentene derivatives toward the A ring of FR182877. Journal of Organic Chemistry, 2004, 69 (13), pp.4555-4558. ⟨10.1021/jo049557d⟩. ⟨hal-00954815⟩