Total syntheses of clausamines A-C and clausevatine D.
The first total syntheses of clausamines A-C and clausevatine D are reported. The key step involves a Diels-Alder reaction between an imine quinone and cyclic diene, allowing for the subsequent construction of the carbazole core in a regiospecific manner. Stereochemistry of the natural products is also discussed.
Lebold
Terry P
TP
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Kerr
Michael A
MA
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D054700:Clausena / Q000737:chemistry*; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D002227:Carbazoles; C528593:clausamine A; C528595:clausamine B; C528596:clausamine C; C528594:clausevatine D