Cyclobutane Amino Acid Analogues of Furanomycin Obtained by a Formal [2+2] Cycloaddition Strategy Promoted by Methylaluminoxane
Cyclobutane Amino Acid Analogues of Furanomycin Obtained by a Formal [2+2] Cycloaddition Strategy Promoted by Methylaluminoxane
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DOI：
10.1021/jo9025258
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发表时间：
2010-02-05
影响因子：
3.6
通讯作者：
Rodriguez, Fernando
中科院分区：
文献类型：
--
作者：
Avenoza, Alberto;Busto, Jesus H.;Rodriguez, Fernando
提出了氨基酸抗生素呋喃霉素的新型构象限制性α-氨基酸类似物的合成和构象分析。该限制涉及顺式稠合的环丁烷和四氢呋喃单元，产生不寻常的2-氧杂双环[3.2.0]庚烷核心，这种核心存在于大量具有生物活性的天然产物中。该合成策略基于作为受体烯烃的2-(酰氨基)丙烯酸酯和作为供体烯烃的2,3-二氢呋喃之间的正式[2 + 2]环加成，由大体积铝衍生的路易斯酸，特别是甲基铝氧烷(MAO)促进。此外，按照相同的策略，报道了掺入2-氧杂双环[4.2.0]辛烷的呋喃霉素类似物的合成。
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.