667419-26-3

Upstream product

• 52010-98-7 3-(hydroxymethyl)benzaldehyde 
• 626-19-7 Isophthalaldehyde 
• 83816-41-5 allenyl boronic acid 
• 667419-25-2 3-formylbenzyl benzoate 

Downstream Products

• 667419-39-8 benzoic acid 3-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-benzyl ester 
• 667419-36-5 (2Z,4E,7S)-7-tert-butyldimethylsilyloxy-7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-(tert-butyldimethylsilyloxy)-nona-1,3-dienyl]-2,2-dimethyl-1,3-dioxan-4-yl]]phenylhepta-2,4-dienoic acid ethyl ester 
• 667419-46-7 (2Z,4E)-(S)-7-(3-{(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-phenyl)-7-(1-methoxy-1-methyl-ethoxy)-hepta-2,4-dienoic acid ethyl ester 
• 667419-45-6 (2Z,4E)-(S)-7-(3-{(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-phenyl)-7-hydroxy-hepta-2,4-dienoic acid ethyl ester 
• 667419-35-4 (4R,6R)-4-[3-[(1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl]phenyl]-6-[(1E,3E,8R)-8-(tert-butyldimethylsilyloxy)nona-1,3-dienyl]-2,2-dimethyl-1,3-dioxane 
• 667419-43-4 (4E,6E)-(1R,3R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-1-{3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-dodeca-4,6-diene-1,3-diol 
• 667419-33-2 (1R,11R)-11-(tert-butyldimethylsilyloxy)-1-[3-[(1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl]phenyl]-1-triethylsilyloxy-4-dodecyn-3-one 
• 850005-80-0 (1R,4E,6E,11R)-11-(tert-butyldimethylsilyloxy)-1-[3-[(1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl]phenyl]-1-triethylsilyloxy-4,6-dodecadien-3-one 
• 667419-34-3 (4E,6E)-(1R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-1-{3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-1-hydroxy-dodeca-4,6-dien-3-one 
• 667419-24-1 (3R)-3-[3-[(1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl]phenyl]-N-methoxy-N-methyl-3-triethylsilyloxypropionamide 
• 667419-28-5 (4S)-N-[(3R)-3-[3-((1S)-1-tert-butyldimethylsilyloxy-3-butynyl)phenyl]-3-hydroxypropanoyl]-4-isopropyl-1,3-thiazolidine-2-thione 
• 667419-41-2 3-{3-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-3-hydroxy-N-methoxy-N-methyl-propionamide 
• 667419-40-1 {3-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-methanol 
• 667419-27-4 3-[(1S)-1-(tert-butyldimethylsilyloxy)but-3-ynyl]benzaldehyde 

Relevant academic research and scientific papers

Asymmetric synthesis of macrolactin analogue

Total asymmetric synthesis of macrolactin A analogue was accomplished by the convergent strategy. Rapid access to advanced intermediate 16 through isomerization of ynone to (E,E)-conjugated dienone is a key step of this synthesis. Overall, control of all

Asymmetric synthetic study of macrolactin analogues

We designed two aromatic analogues 1a and 1b of macrolactin A with expectation of enhancing biological activity and metabolical stability. As a result of retrosynthetic analysis of these compounds 1a-b, two synthetic strategies have been examined. The first strategy includes the enantioselective addition of nonadienyl anion, derived from 3, to aldehyde 4 as a key step. The second one includes epimerization of ynone 7 to (E,E)-conjugated dienone 31 and subsequent diastereoselective hydride-reduction of 31. Although the former route furnished no desired target, the latter one was revealed to work well for the synthesis of 1. Unfortunately, the aimed (2Z,4E)-analogue 1a could not be synthesized due to an epimerization of the (2Z)-olefin into the (2E)-olefin. However, these methods could be applied to the total asymmetric synthesis of the (2E,4E)-analogue 1b. Overall, control of all of the four stereocenters was achieved by means of asymmetric and diastereoselective reactions without using any chiral natural sources.