Synthesis of the core ring system of awajanomycin from N-Boc-3-methoxycarbonyl-2-pyridinone

被引：9

作者：

Hiroya, Kou ^{[1
,2
]}

Kawamoto, Kei ^{[1
]}

Inamoto, Kiyofumi ^{[1
]}

Sakamoto, Takao ^{[1
,2
]}

Doi, Takayuki ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, 21st Century COE Program, Comprehens Res & Educ Ctr Planning Drug Dev & Cli, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 18期

关键词：

Awajanomycin; 2-Pyridinone; Silyl ketene acetal; Trimethylaluminum; Conjugate addition; DIELS-ALDER REACTIONS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; LEWIS-ACID; LITHIUM ALLYLDIBUTYLMAGNESATE; NUCLEOPHILIC-ADDITION; OXABICYCLIC ALKENES; HIGHER-ORDER; PIPERIDINES; ORGANOCOPPER;

D O I：

10.1016/j.tetlet.2009.02.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Awajanomycin, which was isolated from marine-derived fungus, possesses unique structural features and cytotoxic activity against A549 cells. Due to its unique structure, no total synthesis has yet been reported, and neither the relative stereochemistry nor the absolute configuration has been determined. We report the synthesis of the core ring system of awajanomycin, which includes: (i) regioselective addition of the acetate unit onto C4-position of N-Boc-3-methoxycarbonyl-2-pyridinone; (ii) stereoselective installation of a hydroxyl group on C3-position; and (iii) stereo- and regioselective epoxide-opening reaction by Me3Al. (c) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2115 / 2118

页数：4

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