434938-13-3

Upstream product

• 434938-20-2 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-[(S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethoxycarbonyl]-but-3-enyl ester 
• 434938-19-9 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester 
• 434938-21-3 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-[(S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethoxycarbonyl]-but-3-enyl ester 
• 459809-64-4 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-4-((S)-2-methoxycarbonyl-1-methyl-ethoxycarbonyl)-1-methyl-but-3-enyl ester 
• 434938-18-8 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester 

Downstream Products

• 294198-57-5 (-)-dibenzyl macrosphelide A 

Relevant academic research and scientific papers

Formal total synthesis of macrosphelide (+)-A, effect on macrolactonization depended upon the lactone formation position

Formal total synthesis of (+)-macrosphelide A (1) was achieved based on macrolactonization via path B from a seco-acid (3) and path C from a seco-acid (4). The yield of macrolactonization via paths B and C were 18 and 59%, respectively.

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.