Total Synthesis of (−)-Stemonine

• DOI: 10.1021/ol035368q
• Publication Date: 2003-08-28T05:46:41Z
• Authors: David R. Williams; Khalida Shamim; Jayachandra P. Reddy; George S. Amato; Stephen M. Shaw
• Keywords: Lactones; Alkaloids; Pyrrolidines; Molecular Structure; Cyclization; Stemonaceae; Stereoisomerism; Azepines; 01 natural sciences; Iodine; 0104 chemical sciences

[reaction: see text] An enantioselective total synthesis of (-)-stemonine (1) is reported via a convergent assembly of the acyclic precursor 2. Key transformations include a Staudinger-aza-Wittig reaction to form the central perhydroazepine ring system and an iodine-induced tandem cyclization to construct the pyrrolidino-butyrolactone framework.