Beilstein J. Org. Chem.2018,14, 2461–2467, doi:10.3762/bjoc.14.222
The first synthesis of diterpenoid eunicellane skeletons incorporating a 1,3-cyclohexadiene moiety is presented. Key step is a low-valenttitanium-induced pinacol cyclization that proved to be perfectly diastereoselective. Determination of the relative configuration of the diol was aided by the
carbinols afforded novel allene systems. Our study may be of help towards the total synthesis of solenopodin or klysimplexin derivatives.
Keywords: conformational analysis; lowvalenttitanium; marine natural products; pinacol coupling; ten-membered rings; Introduction
Eunicellane-type diterpenoids share