1417559-92-2

Upstream product

• 1417608-62-8 C₃₇H₅₄O₄SeSi 

Downstream Products

• 1417559-96-6 2-((1R,5R)-2-(((R)-2-((benzyloxy)methyl)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl)methyl)-5-isopropyl-1-methylcyclopent-2-en-1-yl)acetaldehyde 
• 1417559-97-7 (3aS,4R,5aR,6R,9aR)-9a-(benzyloxymethyl)-4-hydroxy-6-isopropyl-3a,5a-dimethyl-3a,4,5,5a,6,7,9,9a-octahydroazuleno-[5,6-b]furan-2(3H)-one 
• 1417560-10-1 (3aS,4S,5aR,6R,9aR)-9a-(benzyloxymethyl)-4-hydroxy-6-isopropyl-3a,5a-dimethyl-3a,4,5,5a,6,7,9,9a-octahydroazuleno-[5,6-b]furan-2(3H)-one 
• 1417559-94-4 (R)-5-( (benzyloxy)methyl)-5-(((4R,5R)-5-(2-hydroxyethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one 

Relevant academic research and scientific papers

Total synthesis of neodolastane diterpenes trichoaurantianolides C and D

The first total synthesis of trichoaurantianolides C and D is described. An enantiocontrolled pathway leads to rapid construction of the tricyclic carbon skeleton and establishes the trans-dimethyl geometry of the quaternary bridgehead carbons via a reduc

Studies of neodolastanes - Synthesis of the tricyclic core of the trichoaurantianolides

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.