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Studies directed toward the synthesis of the massileunicellins. Part 2

✍ Scribed by Yonghai Chai; Zonghong Mou; Matthias C. McIntosh

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 427 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.02.095

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✦ Synopsis

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.

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