1417560-06-5Relevant academic research and scientific papers
Studies of neodolastanes - Synthesis of the tricyclic core of the trichoaurantianolides
Williams, David R.,Pinchman, Joseph R.
, p. 21 - 37 (2013/03/14)
Studies toward the synthesis of trichoaurantianolide C (5) are described. Stille cross-coupling reactions of (E)-and (Z)-β-stannyl-α,β- unsaturated esters with allylic acetate 32 provide for the stereocontrolled formation of nonconjugated 2,5-diene-1-ols. Studies of the asymmetric Sharpless epoxidation are utilized to establish diastereofacial selectivity for the preparation of a crucial C2 tertiary allylic alcohol for subsequent esterification and ring-closing metathesis. SmI2 reductive cyclization of the key butenolide precursor 49 led to formation of the central seven-membered ring of the tricyclic core of the natural product.
