Matsuura Fumiyoshi, Peters René, Anada Masahiro, Harried Scott S, Hao Junliang, Kishi Yoshito
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
J Am Chem Soc. 2006 Jun 14;128(23):7463-5. doi: 10.1021/ja0618954.
A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.
据报道，通过分子内狄尔斯-阿尔德反应作为形成碳大环核心结构的关键步骤，实现了对翼毒素A-C所有可能非对映异构体的统一全合成。发现C34/C35-二醇保护基对分子内狄尔斯-阿尔德反应的外型/内型选择性和外型面选择性均有显著影响。
