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Studies directed toward the synthesis of the massileunicellins. 2
Yonghai Chai1, Zonghong Mou, Matthias C McIntosh
1Dept. of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, USA.
Tetrahedron Letters
|April 9, 2010
Abstract:
The fully substituted hydroisobenzofuran core of the massileunicellins containing 8 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.

