1224952-48-0

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 1446347-55-2 tert-butyl 3-[(1S)-1-methoxy-2-propenyl]phenoxydimethylsilane 
• 1446347-64-3 2-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]acetic acid 
• 1446347-60-9 (2R,3R,4S,7S)-methyl 7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate 
• 106987-88-6 2-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]-1-ethanol 
• 1446347-63-2 [(4R,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methyl-1-benzenesulfonate 
• 1446347-62-1 [(4R,5R)-5-(2-[1-(tert-Butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol 
• 1446347-61-0 ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 1446347-58-5 (2S,3R,4S,7S)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptane-1,3-diol 
• 1446347-57-4 (2S,3R,4S,7S)-7-(3-[1-(tert-butyl)-1,1-dimethylsilyl]oxyphenyl)-1-(2,2-dimethyl-1,1-diphenylpropoxy)-7-methoxy-2,4-dimethylheptan-3-ol 
• 1446347-56-3 (2S,3R,4S,5E,7S)-7-(3-[1-(tert-butyl)-1,1-dimethylsilyl]oxyphenyl)-1-(2,2-dimethyl-1,1-diphenylpropoxy)-7-methoxy-2,4-dimethyl-5-hepten-3-ol 
• 1446347-66-5 (2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate 
• 1446347-53-0 (1S)-1-(3-[1-(tert-butyl)-1,1-dimethylsilyl]oxyphenyl)-2-propen-1-ol 
• 96013-95-5 3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde 

Relevant academic research and scientific papers

Nhatrangin A: Total Syntheses of the Proposed Structure and Six of Its Diastereoisomers

A total synthesis of the proposed structure of nhatrangin A is described. This strategy relies on two aldol reactions to install the chiral centers at C3/C4 and C3′/C4′, a lithium-mediated coupling between an advanced intermediate alkyne and a Weinreb amide to complete the C1-C13 alkyl scaffold, and a Yamaguchi esterification to set the side chain. Discrepancies in the spectroscopic data between synthetic and natural nhatrangins led us to synthesize six more diastereoisomers of the proposed structure of nhatrangin A.

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.

The first total synthesis of nhatrangin A

The first total synthesis of nhatrangin A has been achieved. Pivotal bond forming events in the synthesis include Brown crotylboration, olefin cross-metathesis, Sharpless asymmetric dihydroxylation and Yamaguchi esterification. The Royal Society of Chemis