Stereospecific, enantiospecific total synthesis of the sarpagine indole alkaloids (E)16-epiaffinisine, (E)16-epinormacusine B, and dehydro-16-epiaffinisine.
[reaction: see text] The first stereospecific total synthesis of the sarpagine indole alkaloids (E)16-epiaffinisine (1), (E)16-epinormacusine B (2), and dehydro-16-epiaffinisine (4) has been completed; this method has also resulted in the synthesis of dehydro-16-epinormacusine B (5). The formation of the required ether in both 4 and 5 was realized with complete control from the top face on treatment of the corresponding alcohols with DDQ/THF in 98% and 95% yields, respectively.
Yu
Jianming
J
Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, USA.
Liao
Xuebin
X
Cook
James M
JM
D000470:Alkaloids / Q000138:chemical synthesis*; D026121:Indole Alkaloids / Q000138:chemical synthesis; D007211:Indoles / Q000138:chemical synthesis*; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism; D014197:Trees / Q000737:chemistry; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry
C475968:(E)16-epiaffinisine; C475969:(E)16-epinormacusine B; D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; C475970:dehydro-16-epiaffinisine; C028129:tryptophan methyl ester; D014364:Tryptophan