Total synthesis of (+)-crocacin C

被引:41
作者
Feutrill, JT [1 ]
Lilly, MJ [1 ]
Rizzacasa, MA [1 ]
机构
[1] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia
关键词
D O I
10.1021/ol0064664
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The first asymmetric synthesis of (+)-crocacin C (3) is described which served to confirm the absolute configuration of this compound. The key step in the sequence was the stereoselective assembly of the (E,E)-diene amide side chain by a Stille cross-coupling between the stannane 5 and vinyl iodide 6.
引用
收藏
页码:3365 / 3367
页数:3
相关论文
共 24 条
[1]  
[Anonymous], 1997, ORGANIC REACTIONS
[2]  
BASHA A, 1977, TETRAHEDRON LETT, P4171
[3]   APPLICATION OF THE IBUKA-YAMAMOTO REACTION TO A PROBLEM IN STEREOCHEMICAL COMMUNICATION - A STRATEGY FOR THE STEREOSPECIFIC SYNTHESIS AND STABILIZATION OF THE TRIENE SUBSTRUCTURE OF RAPAMYCIN THROUGH SULFONE SUBSTITUTION [J].
CHEN, SH ;
HORVATH, RF ;
JOGLAR, J ;
FISHER, MJ ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5834-5845
[4]   THE PARA-METHOXYBENZYL GROUP AS PROTECTIVE GROUP OF THE ANOMERIC CENTER - SELECTIVE CONVERSIONS OF HYDROXY-GROUPS INTO BROMO GROUPS IN PARA-METHOXYBENZYL 2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE [J].
CLASSON, B ;
GAREGG, PJ ;
SAMUELSSON, B .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (05) :419-422
[5]   Total synthesis of (-)-reveromycin B [J].
Cuzzupe, AN ;
Hutton, CA ;
Lilly, MJ ;
Mann, RK ;
Rizzacasa, MA ;
Zammit, SC .
ORGANIC LETTERS, 2000, 2 (02) :191-194
[6]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[7]   DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].
EVANS, DA ;
CHAPMAN, KT ;
CARREIRA, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578
[8]   SAMARIUM-CATALYZED INTRAMOLECULAR TISHCHENKO REDUCTION OF BETA-HYDROXY KETONES - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF DIFFERENTIATED ANTI 1,3-DIOL MONOESTERS [J].
EVANS, DA ;
HOVEYDA, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6447-6449
[9]   C-13 NMR CHEMICAL-SHIFT CORRELATIONS IN 1,3-DIOL ACETONIDES - IMPLICATIONS FOR THE STEREOCHEMICAL ASSIGNMENT OF PROPIONATE-DERIVED POLYOLS [J].
EVANS, DA ;
RIEGER, DL ;
GAGE, JR .
TETRAHEDRON LETTERS, 1990, 31 (49) :7099-7100
[10]   LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].
FARINA, V ;
KRISHNAN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595