Total Synthesis of Bafilomycin A1

被引：60

作者：

Kleinbeck, Florian ^{[1
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, HCI H335, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 03期

基金：

瑞士国家科学基金会;

关键词：

acetylides; asymmetric synthesis; natural products; nitrile oxides; total synthesis; PRACTICAL CHIRAL AUXILIARY; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; PROPARGYLIC ALCOHOLS; TERMINAL ALKYNES; ALDOL REACTIONS; FRAGMENT; REDUCTION; MACROLIDE; ALDEHYDES;

D O I：

10.1002/anie.200804645

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent synthesis of bafilomycin A1 (see structure) is presented, and relies on the Zn(OTf)2-mediated diastereoselective addition of alkynes to aldehydes. The coupling of a complex enyne with a sensitive aldehyde in the key step, in combination with a novel strategy for a chemoselective trans-reduction of the enyne, establishes an alternative to standard palladium-catalyzed cross-coupling strategies for the formation of 1,3-dienes. (Chemical Equation Presented). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：578 / 581

页数：4

共 60 条

[1] The anti-selective boron-mediated asymmetric aldol reaction of carboxylic esters [J].

Abiko, A ;

Liu, JF ;

Masamune, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (10) :2586-2587

[2] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].

Anand, NK ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688

[3] 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

[4]

Bode JW, 2001, ANGEW CHEM INT EDIT, V40, P2082, DOI 10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO

[5]

2-1

[6] V-ATPases as drug targets [J].

Bowman, EJ ;

Bowman, BJ .

JOURNAL OF BIOENERGETICS AND BIOMEMBRANES, 2005, 37 (06) :431-435

[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] Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions [J].

Boyall, D ;

Frantz, DE ;

Carreira, EM .

ORGANIC LETTERS, 2002, 4 (15) :2605-2606

[9] Diastereoselective hydroformylation of acyclic olefins:: Efficient construction of an all-anti stereotriade building block for polyketide synthesis [J].

Breit, B ;

Zahn, SK .

TETRAHEDRON LETTERS, 1998, 39 (14) :1901-1904

[10] STEREOCHEMISTRY OF THE HYGROLIDINS [J].

COREY, EJ ;

PONDER, JW .

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

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