Journal of Organic Chemistry p. 4023 - 4028 (1986)
Update date:2022-08-05
Topics:
Parker, Kathlyn A.
Farmar, James G.
The stereoselective synthesis of dl-biflora-4,10(19),15-triene (1), a bicyclic diterpene component of the defense secretion of termite soldiers (Cubitermes umbratus), makes use of the regioselective Ireland-Claisen rearrangement of the Z-enolates of esters of 2,5-disubstituted 1,4-dien-3-ols.The synthetic scheme links the dienol Ireland-Claisen rearrangement with an intramolecular Diels-Alder closure; this strategy allows introduction of the four contiguous chiral centers with the desired relative stereochemistry.
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