604791-32-4

Upstream product

• 604791-30-2 (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptane-1,3-diol 
• 604791-29-9 {(2S,3S)-3-[(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-butyl]-oxiranyl}-methanol 
• 604791-28-8 (E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hept-2-enoic acid ethyl ester 
• 604791-15-3 (E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hept-2-en-1-ol 
• 124356-91-8 (4S,2'S,3'R)-3-(2'-methyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone 
• 145937-05-9 (2S,3R)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide 
• 604791-31-3 tert-Butyl-{(1R,2R)-1-ethyl-2-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propoxy}-dimethyl-silane 

Relevant academic research and scientific papers

Synthetic studies directed toward the total synthesis of dolabriferol

Herein we report our results towards the total synthesis of (-)-dolabriferol, describing the synthesis of fragments C1-C9 and C10-C21. This convergent asymmetric approach relies on the use of a common Weinreb amide precursor for the preparation of both fragments, an efficient anti-aldol reaction followed by Zn(BH4)2 reduction to give a 1,3-syn diol, a selective oxidation of a triol under Swern conditions with concomitant lactol formation, and a diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by an efficient epoxide opening with Me2CuCNLi2.