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Total synthesis of (−) altholactone (goniothalenol) from D-glucose

✍ Scribed by Jean-Pierre Gesson; Jean-Claude Jacquesy; Martine Mondon

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
216 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

A ten steps total synthesis of (-) altholactone, enantiomer of an antitumor pyrone isolated from Goniothahw species, is described starting from Dglucose. (+) Altholactone 1 has been isolated in 1977 by LODER et al? from an unknown PotyaZthea species. This substance is characterized by a cis-fused tetrahydrofurano-2 pyrone structure proposed on the basis of spectral data and chemical derivatization. Recently, MCLAUGHLIN et d? have extracted 1 (structure confirmed by X-Ray analysis) from the stem bark of Goniothubmus giganteus Annonceae and subsequently shown that it is cytotoxic in vitro (BS, 9 KB) and active in aiuo against P 388 leukemia. 4 \3 phm 2 HO/' 9 O Ii

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