Studies directed toward the synthesis of the massileunicellins. Part 2
by Chai, Yonghai; Mou, Zonghong; McIntosh, Matt C.
The fully substituted hydroisobenzofuran core of the massileunicellins containing eight contiguous stereocenters was prepared in 12 steps from (S)-(+)-carvone. Noteworthy elements of the synthesis include a one-step oxidative rearrangement/epoxidation, a novel stereoselective directed reduction of a keto diol, and a directed hydrogenation of a congested tetrasubstituted alkene. (C) 2010 Elsevier Ltd. All rights reserved.
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