AN OPTICALLY-ACTIVE CHROMIUM(0)-COMPLEXED BENZALDEHYDE DERIVATIVE IN ORGANIC-SYNTHESIS - A HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-GONIOFUFURONE

被引：36

作者：

MUKAI, C ^{[1
]}

KIM, IJ ^{[1
]}

HANAOKA, M ^{[1
]}

机构：

[1] KANAZAWA UNIV,FAC PHARMACEUT SCI,KANAZAWA,ISHIKAWA 920,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(00)61733-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An antitumor styryl-lactone, (+)-goniofufurone was synthesized in a highly diastereoselective manner from (+)-tricarbonyl(eta6-2-trimethylsilylbenzaldehyde)chromium(0) complex through stereoselective aldol reactions as crucial steps.

引用

页码：6081 / 6082

页数：2

共 12 条

[1] NOVEL BIOACTIVE STYRYL-LACTONES - GONIOFUFURONE, GONIOPYPYRONE, AND 8-ACETYLGONIOTRIOL FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) - X-RAY MOLECULAR-STRUCTURE OF GONIOFUFURONE AND OF GONIOPYPYRONE [J].

FANG, XP ;

ANDERSON, JE ;

CHANG, CJ ;

FANWICK, PE ;

MCLAUGHLIN, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1655-1661

[2]

GRACZA T, 1992, SYNLETT, P191

[3] REGIOSELECTIVE DE-O-BENZYLATION WITH LEWIS-ACIDS [J].

HORI, H ;

NISHIDA, Y ;

OHRUI, H ;

MEGURO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1346-1353

[4] DIASTEREOSELECTIVITY IN THE DIRECTED ALDOL CONDENSATION OF 2-TRIMETHYLSILOXYFURAN WITH ALDEHYDES - A STEREODIVERGENT ROUTE TO THREO-DELTA-HYDROXY-GAMMA-LACTONES AND ERYTHRO-DELTA-HYDROXY-GAMMA-LACTONES [J].

JEFFORD, CW ;

JAGGI, D ;

BOUKOUVALAS, J .

TETRAHEDRON LETTERS, 1987, 28 (35) :4037-4040

[5] AN OPTICALLY-ACTIVE CHROMIUM(0)-COMPLEXED BENZALDEHYDE IN ORGANIC-SYNTHESIS - A HIGHLY STEREOCONTROLLED ASYMMETRIC-SYNTHESIS OF (2R,3S)-(-)-N-BENZOYL-3-PHENYLISOSERINE METHYL-ESTER, THE TAXOL C-13 SIDE-CHAIN ANALOG [J].

MUKAI, C ;

KIM, IJ ;

HANAOKA, M .

TETRAHEDRON-ASYMMETRY, 1992, 3 (08) :1007-1010

[6] A SYNTHESIS OF GONIOFUFURONE [J].

MURPHY, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (16) :1096-1097

[7] NEW TRANSFORMATION OF THIOETHERS INTO ETHERS USING THALLIUM(III) NITRATE [J].

NAGAO, Y ;

KANEKO, K ;

OCHIAI, M ;

FUJITA, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (06) :202-203

[8] ETHOXYCARBONYLMETHYLENETRIPHENYLPHOSPHORANE IN CARBOHYDRATE-CHEMISTRY .2. A SHORT AND EFFICIENT SYNTHESIS OF (+)-GONIOFUFURONE [J].

PRAKASH, KRC ;

RAO, SP .

TETRAHEDRON, 1993, 49 (07) :1505-1510

[9] STEREOCONTROLLED SYNTHESES OF (-)-GONIOFUFURONE AND (-)-8-EPI-GONIOFUFURONE [J].

SHING, TKM ;

TSUI, HC ;

ZHOU, ZH .

TETRAHEDRON, 1992, 48 (40) :8659-8666

[10] GONIOFUFURONE - SYNTHESIS AND ABSOLUTE-CONFIGURATION [J].

SHING, TKM ;

TSUI, HC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (05) :432-434

← 1 2 →