1450899-55-4

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 139165-56-3 threo-(2R,3R)-1-phenyl-2,3-butanediol 
• 1560-06-1 1-phenyl-2-butene 

Downstream Products

• 1450899-63-4 (2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate 

Relevant academic research and scientific papers

Total synthesis of nhatrangin a

A concise and stereoselective approach for the synthesis of key intermediates for aplysiatoxins, oscillatoxins, and nhatrangins and their utility for the total synthesis of nhatrangin A has been demonstrated. The advanced intermediates aromatic aldehyde 11 and dihydroxy acid 12 were synthesized in eight steps (44% overall yield) and three steps (55% overall yield), respectively. An asymmetric Michael addition, CBS reduction, and proline-catalyzed crossed-aldol reactions were utilized as key steps for the generation of all the chirality of main chain hydroxyaldehyde, while the appended side-chain-protected 3,4-dihydroxypentanoic acid was achieved in a shortest route, using Sharpless dihydroxylation, diol protection, and RuO 4-catalyzed aromatic over-oxidation reactions. Synthesis of nhatrangin A was accomplished by coupling of dihydroxy acid 12 with β-hydroxyallyl ester (obtained from 11) under Yamaguchi reaction conditions followed by a one-pot deprotection of all protecting groups.