Total synthesis of (+)-crocacin D.
[structure: see text] The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.
Dias
Luiz C
LC
Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C. P. 6154 Campinas, SP, Brazil. ldias@iqm.unicamp.br
de Oliveira
Luciana G
LG
Vilcachagua
Janaína D
JD
Nigsch
Florian
F
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000475:Alkenes; D000577:Amides; C500920:crocacin A; C500919:crocacin B; C500918:crocacin C; C451481:crocacin D