CONJUGATE ADDITION-ALDOL APPROACH TO THE SIMPLE BICYCLIC-DIYNENE CORE STRUCTURE FOUND IN THE ESPERAMICINS AND CALICHEAMICINS

被引：17

作者：

KADOW, JF

TUN, MM

VYAS, DM

WITTMAN, MD

DOYLE, TW

机构：

[1] Bristol-Myers Squibb Company, Wallingford, CT 06492-7660

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 11期

关键词：

ALDOL; DIMETHYLALUMINUM BENZENE THIOLATE; DIYNENE; ESPERAMICIN CORE; TITANIUM ISOPROPOXIDE;

D O I：

10.1016/S0040-4039(00)91637-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stable 12-beta-hydroxybicyclo[7.1.0] diynene core 15 has been prepared stereospecifically. The key step consists of conjugate addition of dimethylaluminum benzenethiolate to enone aldehyde 12 followed by an in situ titanium isopropoxide assisted aldol cyclization to produce alcohol 13 as a single isomer.

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页码：1423 / 1426

页数：4

相关论文

共 27 条

[1]

DANISHEFSKY SJ, 1989, J ORG CHEM, V54, P2781

[2]

DANISHEFSKY SJ, 1988, J AM CHEM SOC, V110, P6980

[3]

DANISHEFSKY SJ, 1990, J ORG CHEM, V55, P2576

[4]

DANISHEFSKY SJ, 1990, J AM CHEM SOC, V112, P3253

[5] ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .3. STRUCTURES OF ESPERAMICINS-A1, ESPERAMICIN-A2, AND ESPERAMICIN-A1B [J].

GOLIK, J ;

DUBAY, G ;

GROENEWOLD, G ;

KAWAGUCHI, H ;

KONISHI, M ;

KRISHNAN, B ;

OHKUMA, H ;

SAITOH, K ;

DOYLE, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3462-3464

[6] EXPERIMENTAL MODELING OF THE PRIMING MECHANISM OF THE CALICHEAMICIN ESPERAMICIN ANTIBIOTICS - ACTUATION BY THE ADDITION OF INTRAMOLECULAR NUCLEOPHILES TO THE BRIDGEHEAD DOUBLE-BOND [J].

HASELTINE, JN ;

DANISHEFSKY, SJ ;

SCHULTE, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7638-7640

[7] ALDOL REACTION OF ALUMINUM ENOLATE RESULTING FROM 1,4-ADDITION OF R2ALX TO ALPHA,BETA-UNSATURATED CARBONYL COMPOUND - A 1-ACYLETHENYL ANION EQUIVALENT [J].

ITOH, A ;

OZAWA, S ;

OSHIMA, K ;

NOZAKI, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (01) :274-278

[8] CONVERGENT APPROACH TO INTERMEDIATES USED FOR THE SYNTHESIS OF THE ENEDIYNE STRUCTURE OF THE ESPERAMICINS AND CALICHEAMICINS [J].

KADOW, JF ;

SAULNIER, MG ;

TUN, MM ;

LANGLEY, DR ;

VYAS, DM .

TETRAHEDRON LETTERS, 1989, 30 (27) :3499-3500

[9] SYNTHESIS OF A CALICHEAMICIN DEOXYAGLYCONE MODEL BY AN INTRAMOLECULAR ACETYLIDE CYCLIZATION [J].

KENDE, AS ;

SMITH, CA .

TETRAHEDRON LETTERS, 1988, 29 (34) :4217-4220

[10] CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .1. CHEMISTRY AND PARTIAL STRUCTURE OF CALICHEMICIN-GAMMA-1 [J].

LEE, MD ;

DUNNE, TS ;

SIEGEL, MM ;

CHANG, CC ;

MORTON, GO ;

BORDERS, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3464-3466