Cyclobutane Amino Acid Analogues of Furanomycin Obtained by a Formal [2+2] Cycloaddition Strategy Promoted by Methylaluminoxane

被引：26

作者：

Avenoza, Alberto ^{[1
]}

Busto, Jesus H. ^{[1
]}

Canal, Noelia ^{[1
]}

Corzana, Francisco ^{[1
]}

Peregrina, Jesus M. ^{[1
]}

Perez-Fernandez, Marta ^{[1
]}

Rodriguez, Fernando ^{[1
]}

机构：

[1] Univ La Rioja, Dept Quim, Grp Sintesis Quim La Rioja, UA CSIC, E-26006 Logrono, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 03期

关键词：

STEREOSELECTIVE-SYNTHESIS; MOLECULAR-DYNAMICS; ASYMMETRIC-SYNTHESIS; PHOTOCYCLOADDITION REACTION; ENANTIOSELECTIVE SYNTHESIS; PHOTOCHEMICAL-REACTIONS; 1ST SYNTHESIS; DERIVATIVES; SERINE; 2-ACYLAMINOACRYLATES;

D O I：

10.1021/jo9025258

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and conformational analysis of a new type of conformationally restricted alpha-amino acid analogue of the amino acid antibiotic furanomycin is presented. The restriction involves the cis-fused cyclobutane and tetrahydrofuran units, generating the unusual 2-oxabicyclo[3.2.0]heptane core, which is found in a great number of biologically active natural products. The synthetic strategy is based on a formal [2 + 2] cycloaddition between 2-(acylamino)acrylates as acceptor alkenes and 2,3-dihydrofuran as a donor alkene, promoted by bulky aluminum-derived Lewis acids, particularly by methylaluminoxane (MAO). Additionally, following the same strategy, the synthesis of furanomycin analogues incorporating the 2-oxabicyclo[4.2.0]octane is reported.

引用

页码：545 / 552

页数：8

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