Total synthesis of (+)-crocacin D

被引：63
作者：
Dias, LC
de Oliveira, LG
Vilcachagua, JD
Nigsch, F
机构：
[1] Univ Estadual Campinas, Inst Quim, Campinas, SP, Brazil
[2] Ecole Normale Super, Dept Chem, F-75231 Paris, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 06期
关键词：
D O I：
10.1021/jo047732k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
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收藏
页码：2225 / 2234
页数：10
相关论文
共 64 条
[1]   Base assisted substitution of α-amidoalkyl sulfones by nitromethane anion.: A new entry to functionalized α-amino acids. [J].
Ballini, R ;
Petrini, M .
TETRAHEDRON LETTERS, 1999, 40 (23) :4449-4452
[2]   Synthesis of enamides from aldehydes and amides [J].
Bayer, A ;
Maier, ME .
TETRAHEDRON, 2004, 60 (31) :6665-6677
[3]   Total synthesis and biological evaluation of apicularen A and synthetic analogs [J].
Bhattacharjee, A ;
Seguil, OR ;
De Brabander, JK .
TETRAHEDRON LETTERS, 2001, 42 (07) :1217-1220
[4]  
BLOCH R, 1991, SYNLETT, P829
[5]  
BRABANDER JD, 1994, SYNTHESIS-STUTTGART, P855
[6]   SYNTHESIS OF ENAMIDES [J].
BRETTLE, R ;
MOSEDALE, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2185-2195
[7]   Total synthesis of (+)-crocacin A [J].
Chakraborty, TK ;
Laxman, P .
TETRAHEDRON LETTERS, 2003, 44 (27) :4989-4992
[8]   Total synthesis of (+)-crocacin D [J].
Chakraborty, TK ;
Laxman, P .
TETRAHEDRON LETTERS, 2002, 43 (14) :2645-2648
[9]   Total synthesis of (+)-crocacin C [J].
Chakraborty, TK ;
Jayaprakash, S ;
Laxman, P .
TETRAHEDRON, 2001, 57 (46) :9461-9467
[10]  
Chakraborty TK, 2001, TETRAHEDRON LETT, V42, P497, DOI 10.1016/S0040-4039(00)02002-5
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