STEREOCONTROLLED SYNTHESIS OF CALYCULIN-A - CONSTRUCTION OF THE C(1)-C(14) TETRAENE NITRILE UNIT

被引：39

作者：

BARRETT, AGM ^{[1
]}

EDMUNDS, JJ ^{[1
]}

HENDRIX, JA ^{[1
]}

HORITA, K ^{[1
]}

PARKINSON, CJ ^{[1
]}

机构：

[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 17期

关键词：

D O I：

10.1039/c39920001238

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective and geometrically selective synthesis of the C(1)-C(14) tetraene nitrile unit of calyculin A, using aldol chemistry with (+)-(E)-diisopinocampheylborane and Stille coupling, is described.

引用

页码：1238 / 1240

页数：3

共 24 条

[1] THE PREPARATION AND REACTIONS OF 1-LITHIOALKYLAMINO-1-LITHIO-OXY-ALLENE DERIVATIVES [J].

ADLINGTON, RM ;

BARRETT, AGM .

TETRAHEDRON, 1981, 37 (23) :3935-3942

[2]

BARRETT AGM, 1992, J CHEM SOC CHEM COMM

[3]

BASHA A, 1977, TETRAHEDRON LETT, P4171

[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].

BROWN, HC ;

RANDAD, RS ;

BHAT, KS ;

ZAIDLEWICZ, M ;

RACHERLA, US .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2389-2392

[5] CHIRAL SYNTHESIS VIA ORGANOBORANES .7. DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ERYTHRO-BETA-METHYLOMOALLYL AND THREO-BETA-METHYLHOMOALLYL ALCHOLS VIA ENANTIOMERIC (Z)-CROTYLBORANE AND (E)-CROTYLBORANE [J].

BROWN, HC ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5919-5923

[6]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[7] PREPARATION OF TRANS-1,2-BIS(TRI-NORMAL-BUTYLSTANNYL)ETHYLENE [J].

COREY, EJ ;

WOLLENBERG, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (25) :3788-3789

[8]

GREEN TW, 1981, PROTECTIVE GROUPS OR

[9]

GREENE TW, 1991, PROTECTIVE GROUPS OR

[10] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .96. STEREOSELECTIVE SYNTHESIS OF 2,3-DIHYDROXY-4-DIMETHYLAMINO-5-METHOXYPENTANOIC ACID, A FRAGMENT OF CALYCULINS - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF CALYCULINS [J].

HAMADA, Y ;

TANADA, Y ;

YOKOKAWA, F ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1991, 32 (42) :5983-5986

← 1 2 3 →