A convergent approach toward phoslactomycins and leustroducsins

被引：25

作者：

Druais, Valerie ^{[1
]}

Hall, Michael J. ^{[1
]}

Corsi, Camilla ^{[2
]}

Wendeborn, Sebastian V. ^{[2
]}

Meyer, Christophe ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] ESPCI ParisTech, CNRS, UMR 7084, Chim Organ Lab, F-75231 Paris 05, France

[2] Syngenta Crop Protect Muenchwilen AG, CH-4332 Stein, Switzerland

来源：

TETRAHEDRON | 2010年 / 66卷 / 33期

关键词：

Phoslactomycins; Leustroducsins; Metathesis reactions; Noyori reduction; Wittig rearrangement; RING-CLOSING METATHESIS; PROTEIN PHOSPHATASE 2A; ANTIFUNGAL ANTIBIOTICS PHOSLACTOMYCINS; COLONY-STIMULATING FACTORS; ASYMMETRIC TOTAL-SYNTHESIS; FAMILY INDUCE PRODUCTION; METHOXY-N-METHYLAMIDES; MARROW STROMAL CELLS; TUMOR AGENTS CI-920; EFFICIENT SYNTHESIS;

D O I：

10.1016/j.tet.2010.05.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic studies devoted to the development of a convergent approach toward phoslactomycins and leustroducsins, a family of natural products inhibitors of serine/threonine phosphatase 2A, are reported. A formal synthesis of phoslactomycin B was achieved in which the key steps are a [2,3]-Wittig rearrangement to control the C4 and C5 stereocenters, a diastereoselective addition of an acetylenic Grignard reagent to an alpha-alkoxy ketone to create the C8 tertiary alcohol, and a relay ring-closing metathesis to construct the alpha,beta-unsaturated delta-lactone. In this approach, all the stereocenters originate, either directly or indirectly, from catalytic enantioselective reductions of acetylenic ketones. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6358 / 6375

页数：18

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