Stereospecific synthesis of cryptophycin 1

被引：39

作者：

Li, LH ^{[1
]}

Tius, MA ^{[1
]}

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 10期

关键词：

D O I：

10.1021/ol020001r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A brief stereospecific synthesis of cryptophycin I is described in which (R)-mandelic acid serves as the sole source of asymmetry for unit A. The key step is a hetero-Diels-Alder cycloaddition.

引用

页码：1637 / 1640

页数：4

共 36 条

[1] Formal syntheses of cryptophycin A and arenastatin A [J].

Ali, SM ;

Georg, GI .

TETRAHEDRON LETTERS, 1997, 38 (10) :1703-1706

[2]

[Anonymous], [No title captured], Patent No. [US4946835, 4946835]

[3] TOTAL SYNTHESIS OF CRYPTOPHYCINS - REVISION OF THE STRUCTURES OF CRYPTOPHYCIN-A AND CRYPTOPHYCIN-C [J].

BARROW, RA ;

HEMSCHEIDT, T ;

LIANG, J ;

PAIK, S ;

MOORE, RE ;

TIUS, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (09) :2479-2490

[4] Synthesis of 1-aza-cryptophycin 1, an unstable cryptophycin. An unusual skeletal rearrangement [J].

Barrow, RA ;

Moore, RE ;

Li, LH ;

Tius, MA .

TETRAHEDRON, 2000, 56 (21) :3339-3351

[5] Molar scale synthesis of enantiopure stilbene oxide [J].

Chang, HT ;

Sharpless, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6456-6457

[6]

Christopher JA, 2000, SYNLETT, P463

[7] ON THE SCOPE, MECHANISM, AND STEREOCHEMISTRY OF THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF ACTIVATED DIENES WITH ALDEHYDES - AN APPLICATION TO THE ERYTHRONOLIDE PROBLEM [J].

DANISHEFSKY, SJ ;

LARSON, E ;

ASKIN, D ;

KATO, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1246-1255

[8] CHELATION-CONTROLLED FACIALLY SELECTIVE CYCLOCONDENSATION REACTIONS OF CHIRAL ALKOXY ALDEHYDES - SYNTHESES OF A MOUSE ANDROGEN AND OF A CARBON-LINKED DISACCHARIDE [J].

DANISHEFSKY, SJ ;

PEARSON, WH ;

HARVEY, DF ;

MARING, CJ ;

SPRINGER, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1256-1268

[9]

DANISHEFSKY SJ, 1989, CHEMTRACTS, P273

[10] A novel approach for total synthesis of cryptophycins via asymmetric crotylboration protocol [J].

Dhokte, UP ;

Khau, VV ;

Hutchison, DR ;

Martinelli, MJ .

TETRAHEDRON LETTERS, 1998, 39 (48) :8771-8774

← 1 2 3 4 →