Synthesis of (+/-)-bistellettadine A.
Esterification of the trienoic acid with o-xylylene dibromide gave the bis ester that underwent a templated Diels-Alder reaction to afford the macrodiolide stereospecifically in a single step. The synthesis of bistellettadine A was completed in four steps by hydrolysis and side chain elaboration.
Yu
Min
M
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Pochapsky
Susan S
SS
Snider
Barry B
BB
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D002384:Catalysis; D004951:Esterification; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D006146:Guanidines; C547607:bistellettadine A