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

被引：25
|
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
收藏
页码：545 / 552
页数：8
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