604791-14-2

Upstream product

• 604791-26-6 (3R,4R,5S,6S,7R)-2,4,6-Trimethyl-nonane-3,5,7-triol 
• 145937-05-9 (2S,3R)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide 
• 124356-91-8 (4S,2'S,3'R)-3-(2'-methyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone 
• 604791-23-3 (3R,4R,5R,6R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-nonane-3,5-diol 
• 604791-17-5 (3R,4R,6S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4,6-trimethyl-nonan-5-one 
• 159218-06-1 (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-heptan-3-one 

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.