816458-94-3

Upstream product

• 815600-21-6 2-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol 
• 207123-20-4 (S,S)-2,2-dimethyl-4-(tert-butyldimethylsilyloxy)methyl-5-hydroxymethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 

Downstream Products

• 815600-30-7 (2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one 
• 815600-33-0 (2R,3R,4S,5S,6R)-2-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran 
• 815600-22-7 1-[(4S,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propan-1-ol 
• 815600-19-2 1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propan-1-one 

Relevant academic research and scientific papers

Total Synthesis of (-)-Stemoamide by Sequential Overman/Claisen Rearrangement

The enantioselective total synthesis of (-)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.

Synthetic studies on apoptolidin: Synthesis of the C12-C28 fragment via a highly stereoselective aldol reaction

The stereoselective and convergent synthesis of the C12-C28 segment 2 of the apoptosis inducing macrolide antibiotic, apoptolidin (1), is described. The synthesis involves a highly stereoselective tin(II)-mediated aldol reaction between the C17-C22 ethyl