A REMARKABLE GLYCOSYLATION REACTION - THE TOTAL SYNTHESIS OF CALICHEAMICIN GAMMA(1)

被引：46

作者：

HITCHCOCK, SA

CHUMOYER, MY

BOYER, SH

OLSON, SH

DANISHEFSKY, SJ

机构：

[1] SLOAN KETTERING INST CANC RES,BIOORGAN CHEM LAB,NEW YORK,NY 10021

[2] YALE UNIV,DEPT CHEM,NEW HAVEN,CT 06511

[3] COLUMBIA UNIV,DEPT CHEM,NEW YORK,NY 10027

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 21期

关键词：

D O I：

10.1021/ja00126a014

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An account of the reasoning and reduction to practice of a highly convergent total stereospecific synthesis of calicheamicin gamma(1)(I) (1) is provided. The key finding was the use of a very mild promoter system (silver triflate and 4 Angstrom molecular sieves in methylene chloride) to allow for coupling of trichloroacetimidate 21 with advanced calicheamicinone-like accepters (see 17 and 18). Glycosidation with 17 affords a 3:1 ratio of equatorial to axial glycosides. The use of 18 seems to afford only the equatorial beta-glycoside. Remarkably, use of the enantiomer of 17 as the acceptor gave an 18:1 ratio of axial to equatorial product.

引用

页码：5750 / 5756

页数：7

共 30 条

[1] ON THE DNA RECOGNITION ROLE OF THE CARBOHYDRATE SECTOR IN CALICHEAMICIN - A COMPARISON OF DNA-CLEAVING CAPACITY OF ENANTIOMERIC CALICHEAMICINONES
AIYAR, J
HITCHCOCK, SA
DENHART, D
LIU, KKC
DANISHEFSKY, SJ
CROTHERS, DM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (08): : 855 - 858
[2] INTERACTION OF THE ARYL TETRASACCHARIDE DOMAIN OF CALICHEAMICIN-GAMMA-1(I) WITH DNA - INFLUENCE ON AGLYCON AND METHIDIUMPROPYL-EDTA.IRON(II)-MEDIATED DNA CLEAVAGE
AIYAR, J
DANISHEFSKY, SJ
CROTHERS, DM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (19) : 7552 - 7554
[3] BOYER SH, 1994, UNPUB
[4] TOTAL SYNTHESIS OF CALICHEAMICINONE - A SOLUTION TO THE PROBLEM OF THE ELUSIVE URETHANE
CABAL, MP
COLEMAN, RS
DANISHEFSKY, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) : 3253 - 3255
[5] THE ESPERAMICIN-CALICHEAMICIN AGLYCONES - RING-CLOSURE OF A SIMPLE STRAINED SYSTEM MEDIATED BY CHROMIUM(II)-NICKEL(II) SALTS
CREVISY, C
BEAU, JM
[J]. TETRAHEDRON LETTERS, 1991, 32 (27) : 3171 - 3174
[6] A CONCISE ROUTE TO THE CALICHEAMICIN-ESPERAMICIN SERIES - THE CRYSTAL-STRUCTURE OF A CORE SUBUNIT
DANISHEFSKY, SJ
MANTLO, NB
YAMASHITA, DS
SCHULTE, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) : 6890 - 6891
[7] SILVER TRIFLUOROMETHANESULFONATE(TRIFLATE) ACTIVATION OF TRICHLOROACETIMIDATES IN GLYCOSYLATION REACTIONS
DOUGLAS, SP
WHITFIELD, DM
KREPINSKY, JJ
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (01) : 131 - 136
[8] THE CARBOHYDRATE DOMAIN OF CALICHEAMICIN GAMMA-1(I) DETERMINES ITS SEQUENCE SPECIFICITY FOR DNA CLEAVAGE
DRAK, J
IWASAWA, N
DANISHEFSKY, S
CROTHERS, DM
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (17) : 7464 - 7468
[9] TOTAL SYNTHESIS OF CALICHEAMICIN-GAMMA-1(I) .1. SYNTHESIS OF THE OLIGOSACCHARIDE FRAGMENT
GRONEBERG, RD
MIYAZAKI, T
STYLIANIDES, NA
SCHULZE, TJ
STAHL, W
SCHREINER, EP
SUZUKI, T
IWABUCHI, Y
SMITH, AL
NICOLAOU, KC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (17) : 7593 - 7611
[10] SYNTHESIS OF THE CALICHEAMICIN ARYLTETRASACCHARIDE DOMAIN BEARING A REDUCING TERMINUS - COUPLING OF FULLY SYNTHETIC AGLYCONE AND CARBOHYDRATE DOMAINS BY THE SCHMIDT REACTION
HALCOMB, RL
BOYER, SH
DANISHEFSKY, SJ
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (03): : 338 - 340

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