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The first total synthesis of goniothalesdiol

✍ Scribed by Matej Babjak; Peter Kapitán; Tibor Gracza

Book ID
104251909
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
81 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first total synthesis of goniothalesdiol, a dihydroxylated tetrahydrofuran isolated from Goniothalamus borneensis (Annonaceae), and its 7-epimer is described starting with D-mannitol. The key step of these syntheses is palladium(II)-catalyzed oxycarbonylation of unsaturated triols with D-lyxo and D-xylo configuration, respectively, which allowed efficient construction of the tetrahydrofuran ring with excellent threo-selectivity at the newly formed stereogenic centre.

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