Enantioselective Synthesis of (−)-Sclerophytin A by a Stereoconvergent Epoxide Hydrolysis

Wang, Bin; Ramirez, Armando P.; Slade, Justin J.; Morken, James P.

doi:10.1021/ja108185z.s002

ja108185z_si_002.pdf (838.53 kB)

Enantioselective Synthesis of (−)-Sclerophytin A by a Stereoconvergent Epoxide Hydrolysis

journal contribution

posted on 2010-11-24, 00:00 authored by Bin Wang, Armando P. Ramirez, Justin J. Slade, James P. Morken

The cytotoxic natural product (−)-sclerophytin A was constructed in 13 steps from geranial. Highlights from the synthesis are a stereoselective Oshima−Utimoto reaction, a Shibata−Baba indium-promoted radical cyclization, and a novel stereoconvergent epoxide hydrolysis.