132993-03-4Relevant academic research and scientific papers
Stereoselective Access to the Basic Skeleton of Tetracyclic Diterpenes via a Sequence of Consecutive , , and Cycloaddition Reactions
Aubert, Corinne,Gotteland, Jean-Pierre,Malacria, Max
, p. 4298 - 4305 (2007/10/02)
Benzocyclobutenes 9a, 9b, 23, and 24, prepared from 1,5-hexadiyne in good yields in a sequence involving annelation and cycloaddition reactions, underwent an intramolecular reaction to afford the basic skeleton of tetracyclic diterpenes phyllocladane and kaurane.The factors governing the stereochemistry of the Diels-Alder reaction have been elucidated.A carbonyl group at C12 favored the kaurane stereochemistry (58:42) whereas acetal or silylether functions at that same position led to a highly (97:3) or totally stereoselective formation of the phyllocladane ring system.
