Rapid entry into the cryptophycin core via an acyl-β-lactam macrolactonization:: Total synthesis of cryptophycin-24

被引：41

作者：

Eggen, MJ ^{[1
]}

Nair, SK ^{[1
]}

Georg, GI ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 12期

关键词：

D O I：

10.1021/ol010044s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An efficient, concise approach to the macrolide core of the cryptophycins, potent antimitotic agents, has been achieved, The reaction sequence features a novel macrolactonization utilizing a reactive acyl-beta -lactam intermediate that incorporates the p amino acid moiety within the 16-membered macrolide core. This highly modular approach, which allows for multiple alterations throughout the structure, was successfully applied to the total synthesis of cryptophycin-24.

引用

收藏

页码：1813 / 1815

页数：3

相关论文

共 50 条

[1]

ALAWAR RS, 1998, AM ASS CANC RES, P425

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

Ali, SM ;

Georg, GI .

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

[3]

Bai RL, 1996, CANCER RES, V56, P4398

[4] 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

[5] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[6]

Christopher JA, 2000, SYNLETT, P463

[7] Synthesis and in vitro cytotoxicity of cryptophycins and related analogs [J].

deMuys, JM ;

Rej, R ;

Nguyen, D ;

Go, B ;

Fortin, S ;

Lavallee, JF .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (10) :1111-1116

[8] 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

[9] Total synthesis of cryptophycin-24 (Arenastatin A) amenable to structural modifications in the C16 side chain [J].

Eggen, M ;

Mossman, CJ ;

Buck, SB ;

Nair, SK ;

Bhat, L ;

Ali, SM ;

Reiff, EA ;

Boge, TC ;

Georg, GI .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7792-7799

[10] Enantioselective synthesis of a 3′-dephenylcryptophycin synthon [J].

Eggen, MJ ;

Georg, GI .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (22) :3177-3180

← 1 2 3 4 5 →