The enantioselective synthesis of (-)-lycoramine with the Birch-Cope sequence.
The first enantioselective synthesis of (-)-lycoramine has been achieved in 14 steps and 5% overall yield from the biaryl derivative 1. The synthesis applies the previously developed Birch-Cope sequence to create the key arylic quaternary stereocenter of (-)-lycoramine with excellent enantioselective control. The product of the Birch-Cope sequence, a versatile 4,4-disubstituted-2-carboxamide-2-cyclohexen-1-one, was elaborated through an intramolecular conjugate addition of a phenol to create the dihydrofuran ring. Chemoselective elaboration of the allyl group into an amide followed by a modified Pictet-Spengler reaction generated the azepine ring.
Malachowski
William P
WP
Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, USA. wmalacho@brynmawr.edu
Paul
Tapas
T
Phounsavath
Sophia
S
D000438:Alcohols / Q000737:chemistry; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D005702:Galantamine / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D047151:Amaryllidaceae Alkaloids; D001381:Azepines; D005663:Furans; D005702:Galantamine; D006859:Hydrogen; C500482:lycoramine; C039281:furan