Quesnoin, a Novel Pentacyclic ent-Diterpene from 55 Million Years Old Oise Amber

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• 作者：Jean Jossang ; Hakima Bel-Kassaoui ; Akino Jossang ; Mannan Seuleiman ; André ; Nel
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：January 18, 2008
• 年：2008
• 卷：73
• 期：2
• 页码：412 - 417
• 全文大小：326K
• 年卷期：v.73,no.2(January 18, 2008)
• ISSN：1520-6904

文摘

Amber, fossilized tree resin, found at the Oise River area of the Paris basin (France) was dated as being55 million years old. Quesnoin, a novel unique pure organic compound, was isolated from Oise amber.¹H and ¹³C NMR spectroscopic analysis indicated an unknown diterpene skeleton, quesnane. The absoluteconfigurations of the eight chiral centers of quesnoin were determined to be 4S, 5S, 8R, 9S, 10S, 13S,14R, and 16S by chiral auxiliary (R)- and (S)-phenylglycine methyl ester derivatization. Quesnoin allowedus to disclose the tree producer, corresponding to modern Hymenaea oblongifolia, Fabaceae, a subfamilyof Caesalpiniaceae, one of the oldest angiosperm. The presence of the Amazon rainforest tree, H.oblongifolia, indicated that the climate of the Paris basin might have been tropical in the early Eoceneperiod, 55 million years ago.