Total synthesis of xanthanolides

The total synthesis and determination of the absolute configuration of (+)- and (−)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8- epi-xanthatin ( 1), dihydroxanthatin ( 2), and xanthatin ( 3) we...

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Bibliographic Details
Published in:Tetrahedron 2010-10, Vol.66 (43), p.8407-8419
Main Authors: Matsuo, Kazumasa, Ohtsuki, Keiko, Yoshikawa, Takashi, Shishido, Kozo, Yokotani-Tomita, Kaori, Shindo, Mitsuru
Format: Article
Language:English
Subjects:
Acylation
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lactones
Natural products
Organic chemistry
Preparations and properties
Sesquiterpene lactones
Synthesis (chemistry)
Terpenoids
Tetrahedrons
Total synthesis
Xanthanolides
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Summary:The total synthesis and determination of the absolute configuration of (+)- and (−)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8- epi-xanthatin ( 1), dihydroxanthatin ( 2), and xanthatin ( 3) were also prepared, starting from a common intermediate derived from the synthesis of sundiversifolide. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.08.061