459809-62-2

Upstream product

• 183625-29-8 methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 
• 459809-78-0 (E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid methyl ester 
• 294198-48-4 methyl (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoate 
• 294198-49-5 (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid 
• 459809-90-6 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (S)-2-((E)-(1S,2R)-2-benzyloxy-4-methoxycarbonyl-1-methyl-but-3-enyloxycarbonyl)-1-methyl-ethyl ester 
• 459809-71-3 (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester 

Downstream Products

• 294198-57-5 (-)-dibenzyl macrosphelide A 
• 459809-85-9 (-)-(4R,5S)-4-benzyloxy-5-hydroxy-(2E)-hexenoic acid 
• 434938-14-4 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-2-((E)-(1S,2R)-2-benzyloxy-4-carboxy-1-methyl-but-3-enyloxycarbonyl)-1-methyl-ethyl ester 

Relevant academic research and scientific papers

Formal total synthesis of (+)-macrosphelide A based on regioselective hydrolysis using lipase.

Three kinds of seco-macrosphelide A congeners, (4R,5S,10R,11S,15S)-6, (4R,5S,9S,14R,15S)-7 and (3S,8R,9S,14R,15S)-8 were chemically synthesized, and they were exposed to the lipase OF-360 from Candida rugosa to give three hydroxy carboxylic acids, respectively. Macrolactonization of the hydroxy acid (4R,5S,10R,11S)-18 derived from (4R,5S,10R,11S,15S)-6 gave 12-membered lactone (19) in 47% overall yield from 6, while that of the seco-acid (4) derived from (4R,5S,9S,14R,15S)-7 afforded (-)-dibenzyl macrosphelide A (25) in 27% overall yield from 7. Macrolactonization of the hydrolysis product, seco-acid (5) derived from (3S,8R,9S,14R,15S)-8, provided (-)-dibenzyl macrosphelide A (25) (5% overall yield from 8) and 12-membered lactone (19) (20% overall yield from 8) concurrently.