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Synthesis of oxygenated spongiane-type diterpenoids from carvone

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
44
Identifiers
DOI: 10.1016/s0040-4039(02)01891-9

Abstract

Abstract A new diastereoselective approach to oxygenated spongiane diterpenes starting from ( R)-(−)-carvone is described. The carvone is incorporated as the B ring in the final spongiane framework using a B→AB→ABC→ABCD approach, which involves an intramolecular Diels–Alder reaction and the regioselective ring-opening of a dihydrofuran ring as key synthetic steps. The structure of the key intermediate in this approach has been verified by X-ray crystallography.

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