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Total synthesis of the marine sesquiterpenes dactylol and africanol. De novo construction of a cyclooctanoid natural product from cycloheptane precursors

LA Paquette, WH Ham

文献索引:Paquette,L.A.; Ham,W.H. Journal of the American Chemical Society, 1987 , vol. 109, p. 3025

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被引用次数: 60

摘要

Abstract: The total synthesis of the marine sesquiterpenes africanol (1) and dactylol (10) from bicyclo [5.1. O] octane precursors is described. The enone 12 was ketalized and cyclopropanated. Removal of the blocking group, aldol condensation with acetaldehyde, and controlled 1, 2 reduction provided the allylic alcohol Ma. Ortho ester Claisen rearrangement of this alcohol furnished carboxylic acid 16, which was converted ...