566203-47-2

Upstream product

• 566203-40-5 (3R,4S)-3-(4-methoxybenzyloxy)-1-penten-4-yl (3S)-3-hydroxybutanoate 
• 196926-52-0 (4R,5S)-(E)-5-(t-butyl(dimethyl)silyloxy)-4-(β-methoxyethoxy)methoxy-2-hexenoic acid 
• 566203-46-1 (3R,4S)-3-(4-methoxybenzyloxy)-1-penten-4-yl (3S)-3-(tert-butyldimethylsilyloxy)butanoate 
• 566203-43-8 5-(tert-butyl-dimethyl-silanyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid ethyl ester 
• 566203-45-0 (3R,4S)-4-hydroxy-3-(4-methoxybenzyloxy)-1-pentene 
• 132055-83-5 (3R,4S)-4-(tert-butyldimethylsilanyloxy)-pent-1-en-3-ol 
• 212051-17-7 4-methoxybenzyl 2,2,2-trifluoroacetimidate 

Downstream Products

• 566203-48-3 (-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-hydroxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate 
• 172923-77-2 (+)-macrosphelide A 
• 566203-38-1 (7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione 
• 566203-39-2 (-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate 

Relevant academic research and scientific papers

Total Synthesis of Macrosphelides A, B, and E: First Application of Ring-Closing Metathesis for Macrosphelide Synthesis

A new synthetic route for macrosphelides A, B, and E based on ring-closing metathesis (RCM) was established. The substrates for RCM could be synthesized starting from commercially available chiral materials, methyl (S)-lactate and methyl (S)- or (R)-3-hydroxybutyrate, in good overall yields. In the investigation of the key RCM step, it was found that the steric factor around the reaction site significantly affected the reaction rate of macrocyclization. A detailed account regarding this synthetic study is described herein.

New strategy for the total synthesis of macrosphelides A and B based on ring-closing metathesis

(Matrix presented) A new total synthesis of macrosphelides A and B using ring-closing metathesis (RCM) as a macrocyclization step is described. The substrate of the RCM could be synthesized from readily available chiral materials, methyl (S)-(+)-3-hydroxybutyrate and methyl (S)-(-)-lactate, with a high efficiency. The RCM proceeded in the presence of Grubbs' Ru-complex, providing a new effective synthetic route to these natural products.