459809-85-9

Upstream product

• 459809-71-3 (E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid methyl ester 
• 459809-62-2 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-2-((E)-(1S,2R)-2-benzyloxy-4-methoxycarbonyl-1-methyl-but-3-enyloxycarbonyl)-1-methyl-ethyl ester 
• 183625-29-8 methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 
• 294198-49-5 (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid 
• 294198-48-4 methyl (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-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 
• 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 

Downstream Products

• 131771-61-4 (-)-(5R,6S)-5-benzyloxy-6-methyl-5,6-dihydro-2H-pyran-2-one 
• 54826-92-5 (5R,6S)-5,6-dihydro-5-hydroxy-6-methylpyran-2-one 

Relevant academic research and scientific papers

Synthesis of γ- and δ-lactone natural products by employing a trans-cis isomerization/lactonization strategy

Alkaline hydrolysis of 4-hydroxy- or/and 5-hydroxy-(2E)-alkenoate followed by acid treatment gave the corresponding (2E)-alkenoic acids which were subjected to lactone formation reaction without further purification. The crude acids were treated with 2,4,6-trichlorobenzoyl chloride in pyridine to afford ?-lactone or d-lactone, respectively, accompanied by trans-cis isomerization. By this procedure, (±)-(4,5)-trans-5-benzyloxy- 2-hexen-4-olide (90% overall yield), (S)-5-hydroxy-2-penten-4-olide (86% overall yield), (4S,5R)-5- hydroxy-2-hexen-4-olide (86% overall yield), (4R,5S)-5-hydroxy-2-hexen-4-olide (82% overall yield), (S)- parasorbic acid (58% overall yield) and natural product, (5R,7S)-7-hydroxy-2-octen-5-olide (euscapholide: 20% overall yield) were synthesized.

δ-Lactone formation from δ-hydroxy-trans-α,β-unsaturated carboxylic acids accompanied by trans-cis isomerization: synthesis of (-)-tetra-O-acetylosmundalin

(±)-(4,5-anti)-4-Benzyloxy-5-hydroxy-(2E)-hexenoic acid 6 was subjected to δ-lactonization in the presence of 2,4,6-trichlorobenzoyl chloride and pyridine to give the α,β-unsaturated-δ-lactone congener (±)-7 (87% yield) accompanied by trans-cis isomerizat

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.