Concise synthesis of taxol A-ring components: Remote diastereoselective additions of alkenyl lithiums to aldehydes

被引：17

作者：

Frost, C ^{[1
]}

Linnane, P ^{[1
]}

Magnus, P ^{[1
]}

Spyvee, M ^{[1
]}

机构：

[1] UNIV TEXAS,DEPT CHEM & BIOCHEM,AUSTIN,TX 78712

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 51期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(96)02159-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The acid chloride 6 provides access to 7 (R,S and S,S) which upon bromine-lithium exchange undergoes remarkably highly diastereoselective additions to aldehydes; 7 is also readily elaborated into the acetal 10. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9139 / 9142

页数：4

共 27 条

[1] STUDIES TOWARDS THE TOTAL SYNTHESIS OF TAXOIDS SYNTHESIS OF AN A-RING BUILDING UNIT [J].

ARSENIYADIS, S ;

YASHUNSKY, DV ;

DEFREITAS, RP ;

DORADO, MM ;

TOROMANOFF, E ;

POTIER, P .

TETRAHEDRON LETTERS, 1993, 34 (07) :1137-1140

[2]

ASTON PR, 1996, SYNTHESIS-STUTTGART, P930

[3]

BAUTA W, 1995, TETRAHEDRON LETT, V36, P5327, DOI 10.1016/00404-0399(50)1083T-

[4]

Boa A. N., 1994, Contemp. Org. Syn, V1, P47, DOI [10.1039/co9940100047, DOI 10.1039/CO9940100047]

[5]

COREY EJ, 1973, TETRAHEDRON LETT, V14, P4499

[6] Total synthesis of baccatin III and taxol [J].

Danishefsky, SJ ;

Masters, JJ ;

Young, WB ;

Link, JT ;

Snyder, LB ;

Magee, TV ;

Jung, DK ;

Isaacs, RCA ;

Bornmann, WG ;

Alaimo, CA ;

Coburn, CA ;

DiGrandi, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :2843-2859

[7]

DOI T, 1994, TETRAHEDRON LETT, V35, P1481, DOI 10.1016/S0040-4039(00)76737-2

[8] AN ENANTIOSELECTIVE APPROACH TO RING A OF TAXOL USING THE WIELAND-MIESCHER KETONE [J].

GOLINSKI, M ;

VASUDEVAN, S ;

FLORESCA, R ;

BROCK, CP ;

WATT, DS .

TETRAHEDRON LETTERS, 1993, 34 (01) :55-58

[9]

KATRITZKY AR, 1995, COMPREHENSIVE ORGANI, V3, P239

[10] SYNTHESIS OF A TAXANE TRIENE [J].

KENDE, AS ;

JOHNSON, S ;

SANFILIPPO, P ;

HODGES, JC ;

JUNGHEIM, LN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3513-3515

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