131934-87-7Relevant academic research and scientific papers
Synthetic studies on basmane diterpenes. enantiospecific total synthesis of (+)-7,8-epoxy -2-basmen-6-one by claisen ring expansion
Paquette, Leo A.,Kang, Ho-Jung
, p. 2610 - 2621 (2007/10/02)
The first of an is described. The enantiospecific pathway by transforming optically pure aldehyde 10 into bicyclic 39. Methylenation of 39 by of the Tebbe reaction allows for opration of a Claisen that completely by way of transition 44 to the 42. Regiospecific cyclopentannulation with installation of four additional stereogenic centers rested upon sucessful introduction of a functionalized four-carbon chain as in 48, facially controlled hydrogenation of the conjugated double bond, cyclization, and hydroxyl-directed epoxidation. Finally, Swern oxidation led to the target molecule 3, whose three-dimensional structural features confirmed by X-ray crystallography.
