Core structure of eremophilanes and bakkanes through niobium catalyzed Diels-Alder reaction: synthesis of (+/-)-bakkenolide A.
A suitable intermediate for the synthesis of eremophilanes and bakkanes was prepared by a highly regioselective and stereoselective one-step synthesis through a niobium catalyzed Diels-Alder reaction. As a demonstration of the versatility of this intermediate, a total synthesis of (+/-)-bakkenolide A is described.
Constantino
Mauricio G
MG
Departamento de Química, Faculdade de Filosofia Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida dos Bandeirantes, 3900, 14040-901, Ribeirão Preto, SP, Brazil. mgconsta@usp.br
Oliveira
Kleber T de
KT
Polo
Ellen C
EC
Silva
Gil V J da
GV
Brocksom
Timothy J
TJ
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009556:Niobium / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013237:Stereoisomerism
D009281:Naphthalenes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C018286:eremophilane compounds; D009556:Niobium; D015107:4-Butyrolactone; C016257:bakkenolide A