1026455-24-2

Upstream product

• 5470-84-8 4-benzyloxybutanal 
• 112482-35-6 1-(benzyloxy)-4,5-epoxypentane 
• 127793-67-3 (R)‐7‐(benzyloxy)hept‐1‐en‐4‐ol 
• 1309595-73-0 (R)-7-(benzyloxy)-4-((4-methoxybenzyl)oxy)hept-1-ene 
• 83458-92-8 ((2R,3R)-3-(3-(benzyloxy)propyl)oxiran-2-yl)methanol 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 198481-99-1 (-)-salicylihalamide A 
• 198482-00-7 salicylihalamide B 
• 507480-22-0 (E)-(7S,9R,10S)-9-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-7-(3-hydroxy-propyl)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one 
• 1309595-76-3 (2R,3S,5R)-8-(benzyloxy)-3,5-bis((4-methoxybenzyl)oxy)-2-methyloctanal 
• 1309595-75-2 C₃₃H₄₂O₅ 
• 1332361-68-8 C₃₅H₄₆O₆ 

Relevant academic research and scientific papers

A new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones via palladium-catalyzed coupling of thioesters

In this paper, we describe a new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones. By exploiting palladium-catalyzed coupling of thioesters with terminal alkynes or alkenylboronic acids, a variety of β-hydroxy ynones or enones, respectively, could be prepared in an efficient manner under mild conditions. AgOTf-promoted intramolecular oxa-conjugate cyclization of β-hydroxy ynones provided 2,6-substituted dihydropyrones in excellent yields. On the other hand, acid-catalyzed cyclization of β-hydroxy enones caused racemization of the product 2,6-substituted tetrahydropyrones due to its reversible nature. Eventually, stereoselective hydrogenation of substituted dihydropyrones was found to be a solid and efficient approach for the synthesis of 2,6-cis-substituted tetrahydropyrone derivatives.

Highly demanding cross-metathesis in the synthesis of the C16-C30 fragment of dolabelide C

A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.

Enantioselective total synthesis of salicylihalamides A and B

We have devised a total synthesis of (12R,13S,15R) salicylihalamides A and B, which allowed revision of the absolute stereochemistry of the natural compounds. The same strategy was then applied to the preparation of naturally occurring salicylihalamides.