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Total synthesis of (+)-altholactone

โœ Scribed by Sung Ho Kang; Wan Joo Kim

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
281 KB
Volume
30
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

+tAltholactone 1, an antitumor agent isolated from GoniothaZamus species, has been synthesized starting from L-glyceraldehyde acetonide. (+I-Altholactone 1 from an unknown PoZyathea species has a novel phenyltetrahydrofurano-2pyrone structure rare for natural compounds .I It turned out to be identical with goniothalenol from the stem bark of Goniothalamus giganteus Annonaceae, which displays cytotoxicity in vitro (BS, 9K.B) and inhibitory activity in vivo against P 388 leukemia.2 Several bioactive 2-pyrones from

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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 te

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Altholactone 1 and (+)-7-epi-altholactone 3 were constructed from Dgulonolactone whereas their respective enantiomers (-)-altholactone 2 and (-)J-epialtholactone 4 were synthesised from D-mannose, involving stereocontrolled reduction of the lactols 21 and 12 as a key step. 'I-epi-altholactone 3, an