Total synthesis of cribrostatin IV: Fine-tuning the character of an amide bond by remote control

被引:95
作者
Chan, C
Heid, R
Zheng, SP
Guo, JS
Zhou, BS
Furuuchi, T
Danishefsky, SJ
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
[2] Mem Sloan Kettering Canc Ctr, Bioorgan Chem Lab, New York, NY 10021 USA
关键词
D O I
10.1021/ja050203t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the enantioselective total synthesis of cribrostatin IV (1). Key features of this synthesis involve the convergent coupling of two highly functionalized homochiral components followed by a lynchpin" Mannich cyclization to establish the pentacyclic core (cf. 19 → 20). Copyright © 2005 American Chemical Society."
引用
收藏
页码:4596 / 4598
页数:3
相关论文
共 33 条
[1]  
BEEBY PJ, 1977, TETRAHEDRON LETT, V18, P3379
[2]   ASYMMETRIC ELECTROPHILIC SUBSTITUTION ON PHENOLS .1. ENANTIOSELECTIVE ORTHO-HYDROXYALKYLATION MEDIATED BY CHIRAL ALKOXYALUMINUM CHLORIDES [J].
BIGI, F ;
CASIRAGHI, G ;
CASNATI, G ;
SARTORI, G ;
FAVA, GG ;
BELICCHI, MF .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5018-5022
[3]   SYNTHESIS OF ISOQUINOLINES .8. 3,4,11,11A-TETRAHYDRO-1H-BENZO[B]QUINOLIZIN-2(6H)-ONES [J].
BOBBITT, JM ;
MOORE, TE .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (07) :2958-&
[4]   SYNTHESIS OF ISOQUINOLINES .7. 4-HYDROXY-1,2,3,4-TETRAHYDROISOQUINOLINES [J].
BOBBITT, JM ;
SIH, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (02) :856-&
[5]   PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
FEASTER, JE ;
NUGENT, WA ;
HARLOW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138
[6]   Reduction potentials of quinones II The potentials of certain derivatives of benzoquinone, naphthoquinone and anthraquinone [J].
Conant, JB ;
Fieser, LF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1924, 46 :1858-1881
[7]   Enantioselective total synthesis of ecteinascidin 743 [J].
Corey, EJ ;
Gin, DY ;
Kania, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9202-9203
[8]  
DANISHEFSKY SJ, 1995, SYNLETT, P475
[9]   A PERIODONIUM TRIFLUOROMETHANESULFONATE - AN ISOLABLE 10-1-4 ORGANOIODINE SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (03) :902-903
[10]   Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].
Fujii, A ;
Hashiguchi, S ;
Uematsu, N ;
Ikariya, T ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522