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Studies directed toward the synthesis of the massileunicellins. 2.

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.

SUBMITTER: Chai Y

PROVIDER: S-EPMC3111956 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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Studies directed toward the synthesis of the massileunicellins. 2.

Chai Yonghai Y Mou Zonghong Z McIntosh Matthias C MC

Tetrahedron letters 20100501 16

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. ...[more]

PMID: 20376298

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