Total synthesis and absolute configuration of the novel microtubule-stabilizing agent peloruside A

被引：116

作者：

Liao, XB ^{[1
]}

Wu, YS ^{[1
]}

De Brabander, JK ^{[1
]}

机构：

[1] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75390 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 14期

关键词：

antitumor agents; configuration determination; cyclization; natural products; total synthesis;

D O I：

10.1002/anie.200351145

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unique configuration-dependent mechanistic switch, observed when epimeric seco-acids are subjected to typical Mitsunobu lactonization conditions, is just one of the many unexpected, yet insightful surprises of a synthetic adventure culminating in the first enantioselective total synthesis of the novel microtubule-stabilizing natural product peloruside A (1).

引用

页码：1648 / 1652

页数：5

共 28 条

[11] Total synthesis of bryostatin 2 [J].

Evans, DA ;

Carter, PH ;

Carreira, EM ;

Charette, AB ;

Prunet, JA ;

Lautens, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7540-7552

[12] A stereochemical model for merged 1,2- and 1,3-asymmetric induction in diastereoselective Mukaiyama aldol addition reactions and related processes [J].

Evans, DA ;

Dart, MJ ;

Duffy, JL ;

Yang, MG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4322-4343

[13]

Hood KA, 2001, ANTI-CANCER DRUG DES, V16, P155

[14]

Hood KA, 2002, CANCER RES, V62, P3356

[15] SYNTHESIS OF BRYOSTATIN-7 [J].

KAGEYAMA, M ;

TAMURA, T ;

NANTZ, MH ;

ROBERTS, JC ;

SOMFAI, P ;

WHRITENOUR, DC ;

MASAMUNE, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7407-7408

[16] REDUCTION OF NATURAL ENONES IN PRESENCE OF CERIUM TRICHLORIDE [J].

LUCHE, JL ;

RODRIGUEZHAHN, L ;

CRABBE, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (14) :601-602

[17] Dimethylmalonyltrialkylphosphoranes: New general reagents for esterification reactions allowing controlled inversion or retention of configuration on chiral alcohols [J].

McNulty, J ;

Capretta, A ;

Laritchev, V ;

Dyck, J ;

Robertson, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1597-1600

[18] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[19] Toward the synthesis of peloruside A:: Fragment synthesis and coupling studies [J].

Paterson, I ;

Di Francesco, ME ;

Kühn, T .

ORGANIC LETTERS, 2003, 5 (04) :599-602

[20] ANALYSIS OF 2 C-13 NMR CORRELATIONS FOR DETERMINING THE STEREOCHEMISTRY OF 1,3-DIOL ACETONIDES [J].

RYCHNOVSKY, SD ;

ROGERS, B ;

YANG, G .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (13) :3511-3515

← 1 2 3 →