Stereoselective synthesis of 3-aryloctahydroindoles and application in a formal synthesis of (-)-pancracine.
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.
Pansare
Sunil V
SV
Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada A1B 3X7. spansare@mun.ca
Lingampally
Rajinikanth
R
Kirby
Raie Lene
RL
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; C511228:pancracine