Stereocontrolled synthesis of (-)-macrolactin A

被引：163

作者：

Marino, JP ^{[1
]}

McClure, MS

Holub, DP

Comasseto, JV

Tucci, FC

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

[2] Univ Sao Paulo, Inst Quim, BR-26077 Sao Paulo, Brazil

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 08期

关键词：

D O I：

10.1021/ja017177t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of (-)-macrolactin A, a 24-membered macrolide, has been achieved using a newly developed 1,3-diol synthon for the introduction of two key stereogenic centers. The synthon was derived from sequential use of the Noyori asymmetric reduction followed by chiral sulfoxide methodology. Tellurium-derived cuprate organometallics offered an efficient and highly stereoselective means for installation of the C8 Z/E-diene, while the C15 E/E-segment was derived from a Julia-Lythgoe olefination. Yamaguchi lactonization was used to secure the macrocycle in a convergent approach with the longest linear sequence of 19 steps from Noyori alcohol 6.

引用

页码：1664 / 1668

页数：5

共 43 条

[1] OPTICALLY ACTIVE SULFOXIDES . SYNTHESIS + ROTATORY DISPERSION OF SOME DIARYL SULFOXIDES [J].

ANDERSEN, KK ;

FOLEY, JW ;

GAFFIELD, W ;

PAPANIKOLAU, NE ;

PERKINS, RI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5637-+

[2]

BENVEGNU T, 1994, SYNLETT, P505

[3] Stereoselective synthesis of macrolactin A analogues .2. The C-1-C-14 fragment [J].

Benvegnu, TJ ;

Gree, RL .

TETRAHEDRON, 1996, 52 (36) :11821-11826

[4] Sequential sp(2)-sp(2) coupling reactions in polyene macrolide synthesis. A novel approach to macrolactin A [J].

Boyce, RJ ;

Pattenden, G .

TETRAHEDRON LETTERS, 1996, 37 (20) :3501-3504

[5] A PRACTICAL AND GENERAL ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PROPA-1,2-DIENYL AND PROPARGYL CARBINOLS [J].

COREY, EJ ;

YU, CM ;

LEE, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :878-879

[6] ZINC-COMPLEXES OF CHIRAL PHENOLS AS CATALYSTS FOR ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES [J].

COREY, EJ ;

HANNON, FJ .

TETRAHEDRON LETTERS, 1987, 28 (44) :5237-5240

[7] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[8] Lewis base activation of Lewis acids: Catalytic enantioselective allylation and propargylation of aldehydes [J].

Denmark, SE ;

Wynn, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :6199-6200

[9] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[10] MODEL STUDIES TOWARD THE SYNTHESIS OF MACROLACTIN-A - ORGANOIRON METHODOLOGY FOR INTRODUCTION OF THE C1-C-11 AND C16-C24 SEGMENTS [J].

DONALDSON, WA ;

BELL, PT ;

WANG, Z ;

BENNETT, DW .

TETRAHEDRON LETTERS, 1994, 35 (32) :5829-5832

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