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A novel approach for construction of the naturally occurring dihydroagarofuran sesquiterpene skeleton

✍ Scribed by Wu Jiong Xia; De Run Li; Lei Shi; Yong Qiang Tu

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
168 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A general and efficient approach for the synthesis of a kind of dihydrofuran sesquiterpenes extensively present in the Celastraceae family of plants has been developed by a series of transformations from santonin. The key creative and versatile steps involve the strategic acid-catalyzed double-bond shifting affording 6, the novel base-promoted epoxide rearrangement of 7 generating two key functions (the C5 OH and the D 7,11 double bond) and the stereoselective construction of a tetrahydrofuran moiety without particularly controlling the stereochemistry of C7. In particular, this approach can introduce any number of hydroxyls at the required positions for synthesis of many natural dihydroagarofuran sesquiterpenes.

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