Improved biomimetic total synthesis of D,L-stephacidin A.
The direct conversion of beta-hydroxyproline derivatives into 5-hydroxypyrazin-2(1H)-ones under Mitsunobu conditions has been discovered to be a general biomimetic protocol generating IMDA intermediates and has been applied to the concise, biomimetic total syntheses of D,L-stephacidin A and D,L-brevianamide B.
Greshock
Thomas J
TJ
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA.
Williams
Robert M
RM
D006909:Hydroxyproline / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011719:Pyrazines / Q000737:chemistry; D013237:Stereoisomerism
D026121:Indole Alkaloids; D011719:Pyrazines; C470895:stephacidin A; D006909:Hydroxyproline