S. Pansare, Rajinikanth Lingampally, Raie Lene Kirby
Jan 7, 2010
Citations
1
Influential Citations
37
Citations
Journal
Organic letters
Abstract
A stereoselective synthesis of 3-aryloctahydroindoles from enantiomerically enriched gamma-nitroketones has been developed. Reduction of imines derived form the nitroketones provides the trans-fused octhaydroindole motif selectively. The cis-octahydroindole skeleton is accessible by an invertive cyclization strategy involving a diastereomerically pure nitromesylate intermediate. This approach was employed in the synthesis of an advanced intermediate to (-)-pancracine. The gamma-nitroketone starting materials are readily available via an organocatalytic Michael reaction.