Total synthesis of bafilomycin A1 relying on iterative 1,2-induction in acyclic precursors

被引：76

作者：

Hanessian, S ^{[1
]}

Ma, JG ^{[1
]}

Wang, WG ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2001年 / 123卷 / 42期

关键词：

D O I：

10.1021/ja011452u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.

引用

页码：10200 / 10206

页数：7

共 73 条

[1] THE CONFORMATIONAL-ANALYSIS OF BAFILOMYCIN-A1 [J].

BAKER, GH ;

BROWN, PJ ;

DORGAN, RJJ ;

EVERETT, JR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (08) :1073-1079

[2] A CONFORMATIONAL STUDY OF BAFILOMYCIN-A1 BY X-RAY CRYSTALLOGRAPHY AND NMR TECHNIQUES [J].

BAKER, GH ;

BROWN, PJ ;

DORGAN, RJJ ;

EVERETT, JR ;

LEY, SV ;

SLAWIN, AMZ ;

WILLIAMS, DJ .

TETRAHEDRON LETTERS, 1987, 28 (45) :5565-5568

[3] CHEMISTRY OF UNUSUAL MACROLIDES .1. PREPARATION OF THE AGLYCONS OF CONCANAMYCIN-A AND ELAIOPHYLIN [J].

BINDSEIL, KU ;

ZEECK, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5487-5492

[4] RING-OPENING OF A CARBOHYDRATE TRIFLATE TO FORM AN ACYCLIC ALKENE [J].

BINKLEY, RW .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (05) :771-775

[5] PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].

BODEN, EP ;

KECK, GE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395

[6] CATECHOL BORON HALIDES - MILD AND SELECTIVE REAGENTS FOR CLEAVAGE OF COMMON PROTECTING GROUPS [J].

BOECKMAN, RK ;

POTENZA, JC .

TETRAHEDRON LETTERS, 1985, 26 (11) :1411-1414

[7] BAFILOMYCINS - A CLASS OF INHIBITORS OF MEMBRANE ATPASES FROM MICROORGANISMS, ANIMAL-CELLS, AND PLANT-CELLS [J].

BOWMAN, EJ ;

SIEBERS, A ;

ALTENDORF, K .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (21) :7972-7976

[8]

CALTER MA, 1993, THESIS HARVARD U

[9]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[10] STEREOCHEMISTRY OF THE HYGROLIDINS [J].

COREY, EJ ;

PONDER, JW .

TETRAHEDRON LETTERS, 1984, 25 (39) :4325-4328

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