作为潜在抗肿瘤药物的环辛烯酮和环辛二烯酮的首次对映选择性全合成及构型确定
First enantioselective total synthesis and configurational assignments of suberosenone and suberosanone as potential antitumor agents.
作者信息
Kousara Mohammad, Ferry Angélique, Le Bideau Franck, Serré Kathalyn L, Chataigner Isabelle, Morvan Estelle, Dubois Joëlle, Chéron Monique, Dumas Françoise
机构信息
CNRS-BioCIS UMR 8076, Chimie des Substances Naturelles, IPSIT and LabEx LERMIT, Faculté de Pharmacie, Université de Paris Sud, 5, rue J.-B. Clément, 92296 Châtenay-Malabry, France.
出版信息
Chem Commun (Camb). 2015 Feb 25;51(16):3458-61. doi: 10.1039/c4cc10041g.
The first enantioselective total syntheses of two marine sesquiterpenes (1R)-suberosenone and (1R)-suberosanone are achieved leading to revision of the AC of natural (1S)-suberosanone. Key elements of the synthesis include hyperbaric asymmetric Michael addition and highly efficient silver trifluoroacetate mediated α-alkylation for the formation of ring A.
首次实现了两种海洋倍半萜（1R）-苏贝罗烯酮和（1R）-苏贝罗沙酮的对映选择性全合成，从而修正了天然（1S）-苏贝罗沙酮的绝对构型。合成的关键步骤包括高压不对称迈克尔加成以及高效的三氟乙酸银介导的α-烷基化反应以构建A环。
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