Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B.
Concise asymmetric total syntheses of the fungal metabolites (-)-stephacidin A, (+)-stephacidin B, and (+)-notoamide B are described. Key features of these total syntheses include (1) a facile synthesis of (R)-allyl proline methyl ester, (2) a revised route toward the pyranoindole ring system, (3) a novel cross-metathesis strategy for the introduction of important functional groups, and (4) an SN2' cyclization to form the [2.2.2] bridged bicyclic ring system. Furthermore, our synthesis has taken advantage of microwave heating to shorten reaction times as well as increase yields for the preparation of vital intermediates.
Artman
Gerald D
GD
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Grubbs
Alan W
AW
Williams
Robert M
RM
D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D026121:Indole Alkaloids; C520596:notoamide B; C470895:stephacidin A; C470894:stephacidin B