917871-10-4

Upstream product

• 92817-88-4 (2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 95514-03-7 (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester 
• 95514-04-8 (R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol 
• 24074-26-8 ethyl (diisopropylphosphoryl)acetate 

Downstream Products

• 164907-39-5 (4R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-4-methylpentan-1-ol 
• 161807-14-3 (-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene 
• 1352125-86-0 (1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4⁽⁵⁾-ene 
• 1352126-06-7 C₃₃H₄₄O₄Si 
• 917871-09-1 (4R)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenal 
• 917871-11-5 (R)-(E)-(+)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol 

Relevant academic research and scientific papers

Studies culminating in the total synthesis and determination of the absolute configuration of (-)-saudin

A full account of studies that culminated in the total synthesis of both antipodes and the assignment of its absolute configuration of Saudin, a hypoglycemic natural product. Two approaches are described, the first proceeding though bicyclic lactone intermediates and related second monocyclic esters. The former was obtained via asymmetric Diels-Alder cycloaddition and the latter by an asymmetric annulation protocol. Both approaches employ a Lewis acid promoted Claisen rearrangement, with the successful approach taking advantage of bidentate chelation to control the facial selectivity of the key Claisen rearrangement.

Formal total synthesis of (-)-spongidepsin

The formal total synthesis of (-)-spongidepsin is described. Three fragments I, II, and III were first prepared from readily available starting materials and then assembled to the target compound. The key steps involved in the synthesis are asymmetric α-hydroxylation, Ender's alkylation, and ring-closing metathesis reactions. An alternative route for the fragment II is also achieved involving Sharpless asymmetric epoxidation and Gilman's alkylation as key reactions.

Stereoselective formal total synthesis of the cyclodepsipeptide (-)-spongidepsin

The formal total synthesis of (-)-spongidepsin is achieved starting from easily available raw materials involving asymmetric α-hydroxylation, Enders alkylation, and RCM as key reactions.

Palladium- and copper-catalyzed 1,4-additions of organozinc compounds to conjugated aldehydes

Conjugated aldehydes undergo smooth Pd(OAc)2·PPh 3- or Me2CuCNLi2-catalyzed 1,4-addition of dialkylzinc reagents.