Total synthesis of (+)-crocacin C.
The total synthesis of (+)-crocacin C is described. The convergent asymmetric synthesis relies on the use of a regio- and diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by epoxide opening with Me(2)CuCNLi(2) and a Stille cross-coupling between E-vinyl stannane 5 and E-vinyl iodide 6 to establish the (E,E)-dienamide moiety. [structure: see text]
Dias
L C
LC
Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, 13083-970 Campinas, SP, Brazil. ldias@iqm.unicamp.br
de Oliveira
L G
LG
D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011090:Polyenes; C089608:crocacin