Divergent Synthesis of the Co-isolated Mycotoxins Longianone, Isopatulin, and (Z)-Ascladiol via Furan Oxidation

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• 作者：Ioannis N. Lykakis ; Ioannis-Panayotis Zaravinos ; Christos Raptis ; Manolis Stratakis
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：August 21, 2009
• 年：2009
• 卷：74
• 期：16
• 页码：6339-6342
• 全文大小：723K
• 年卷期：v.74,no.16(August 21, 2009)
• ISSN：1520-6904

文摘

Longianone and the biosynthetically related mycotoxins isopatulin and (Z)-ascladiol were prepared following a divergent route from a readily available furan diol. The route toward longianone features an unprecedented TBAF-promoted intramolecular oxa-Michael reaction to a conjugated keto enoate, and the oxidation of dihydrolongianone to longianone with stabilized IBX. The route to isopatulin features a chemoenzymatic synthesis of (Z)-ascladiol, and the regioselective oxidation of (Z)-ascladiol to isopatulin with MnO₂.