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Article

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

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Jean Jossang,^† Hakima Bel-Kassaoui,^† Akino Jossang,*^† Mannan Seuleiman,^‡ and André Nel^§

Laboratoire de Chimie des Substances Naturelles, CNRS UMR5154, Musum National d'Histoire Naturelle, 63 rue Buffon 75005 Paris, France, Laboratoire de Chimie Inorganique et Matriaux Molculaires, U.P.E.S.A. 7071, Universit Pierre et Marie Curie, 4 Place Jussieu, 75252 Paris Cedex 05, France, and Laboratoire d'Entomologie, Musum National d'Histoire Naturelle, 45 rue Buffon, 75005 Paris, France

J. Org. Chem., 2008, 73 (2), pp 412–417

DOI: 10.1021/jo701544k

Publication Date (Web): December 23, 2007

†

Laboratoire de Chimie des Substances Naturelles, Muséum National d'Histoire Naturelle.

Corresponding author. Fax: 33140793135.

‡

Université Pierre et Marie Curie.

Laboratoire d'Entomologie, Muséum National d'Histoire Naturelle.

, jossang@mnhn.fr

Abstract

Amber, fossilized tree resin, found at the Oise River area of the Paris basin (France) was dated as being 55 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 absolute configurations 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 allowed us to disclose the tree producer, corresponding to modern Hymenaea oblongifolia, Fabaceae, a subfamily of 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 Eocene period, 55 million years ago.

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Published In Issue January 18, 2008
Received August 12, 2007

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Article

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

Abstract

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Recommend & Share

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