Enantioselective synthesis of curacin A .1. Construction of C1-C7, C8-C17, and C18-C22 segments

被引：26

作者：

Ito, H

Imai, N

Tanikawa, S

Kobayashi, S

机构：

[1] SCI UNIV TOKYO,FAC PHARMACEUT SCI,SHINJUKU KU,TOKYO 162,JAPAN

[2] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 11期

关键词：

D O I：

10.1016/0040-4039(96)00030-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of curacin A, a novel antimitotic antiproliferative antibiotic, was achieved by the connection of C1-C7, C8-C17, and C18-C22 segments. Enantioselective preparation of each segments were accomplished by asymmetric allylation, chiral synthon method, and asymmetric hydrolysis by using pig liver esterase, respectively.

引用

收藏

页码：1795 / 1798

页数：4

相关论文

共 15 条

[1] SYNTHESIS OF CHIRAL VINYLGLYCINES [J].

BEAULIEU, PL ;

DUCEPPE, JS ;

JOHNSON, C .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4196-4204

[2] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[3] DIASTEREOFACE DISCRIMINATION IN THE ADDITION OF ACETYLIDE TO A CHIRAL ALDEHYDE, LEADING TO A SYNTHESIS OF (+)-DEOXYBIOTIN IN ENANTIOMERICALLY PURE FORM STARTING FROM L-CYSTEINE [J].

FUJISAWA, T ;

NAGAI, M ;

KOIKE, Y ;

SHIMIZU, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5865-5867

[4] STRUCTURE OF CURACIN-A, A NOVEL ANTIMITOTIC, ANTIPROLIFERATIVE, AND BRINE SHRIMP TOXIC NATURAL PRODUCT FROM THE MARINE CYANOBACTERIUM LYNGBYA-MAJUSCULA [J].

GERWICK, WH ;

PROTEAU, PJ ;

NAGLE, DG ;

HAMEL, E ;

BLOKHIN, A ;

SLATE, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1243-1245

[5] BOC-L-DMT-OH AS A FULLY N,S-BLOCKED CYSTEINE DERIVATIVE FOR PEPTIDE-SYNTHESIS BY PRIOR THIOL CAPTURE - FACILE CONVERSION OF N-TERMINAL BOC-L-DMT-PEPTIDES TO H-CYS(SCM)-PEPTIDES [J].

KEMP, DS ;

CAREY, RI .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3640-3646

[6] SYNTHESIS OF 1-O-ACYLGLYCEROL 2,3-CYCLIC PHOSPHATE - DETERMINATION OF THE ABSOLUTE STRUCTURE OF PHYLPA, A SPECIFIC INHIBITOR OF DNA-POLYMERASE ALPHA [J].

KOBAYASHI, S ;

TOKUNOH, R ;

SHIBASAKI, M ;

SHINAGAWA, R ;

MURAKAMIMUROFUSHI, K .

TETRAHEDRON LETTERS, 1993, 34 (25) :4047-4050

[7] THE INFLUENCE OF CHAIN-BRANCHING ON THE STERIC OUTCOME OF SOME OLEFIN-FORMING REACTIONS [J].

KOCIENSKI, PJ ;

LYTHGOE, B ;

WATERHOUSE, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (04) :1045-1050

[8] A STUDY OF STEREOSELECTIVE HYDROLYSIS OF SYMMETRICAL DIESTERS WITH PIG-LIVER ESTERASE [J].

MOHR, P ;

WAESPESARCEVIC, N ;

TAMM, C ;

GAWRONSKA, K ;

GAWRONSKI, JK .

HELVETICA CHIMICA ACTA, 1983, 66 (08) :2501-2511

[9] ABSOLUTE-CONFIGURATION OF CURACIN-A, A NOVEL ANTIMITOTIC AGENT FROM THE TROPICAL MARINE CYANOBACTERIUM LYNGBYA-MAJUSCULA [J].

NAGLE, DG ;

GERALDS, RS ;

YOO, HD ;

GERWICK, WH ;

KIM, TS ;

NAMBU, M ;

WHITE, JD .

TETRAHEDRON LETTERS, 1995, 36 (08) :1189-1192

[10] SYNTHESIS OF COMPOUNDS WITH JUVENILE-HORMONE ACTIVITY .16. STEREOSELECTIVE SYNTHESIS OF METHYL TRANS, TRANS-FARNESOATE AND ITS CONVERSION TO DL-C17-CECROPIA JUVENILE-HORMONE [J].

OHKI, M ;

MORI, K ;

MATSUI, M .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1974, 38 (01) :175-181