646520-62-9

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 80910-01-6 (S)-2-[(4-methoxybenzyloxy)methyl]oxirane 

Downstream Products

• 338799-40-9 Triethyl-[(S)-1-(4-methoxy-benzyloxymethyl)-but-3-ynyloxy]-silane 
• 646520-63-0 (S)-tert-butyl((1-((4-methoxybenzyl)oxy)pent-4-yn-2-yl)oxy)dimethylsilane 
• 338799-41-0 (S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-yn-3-ol 
• 338799-30-7 (Z)-(S)-1-[(2R,3aS,5R,6S,7aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-8-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-oct-4-en-3-one 

Relevant academic research and scientific papers

Total synthesis of four stereoisomers of (5Z,8Z,10E,14Z)-12-hydroxy-17,18-epoxy-5,8,10,14-eicosatetraenoic acid and their anti-inflammatory activities

The four stereoisomers of novel lipid mediator 1, (5Z,8Z,10E,14Z)-12-hydroxy-17,18-epoxy-5,8,10,14-eicosatetraenoic acid, were synthesized from six simple fragments. Triyne 2 was convergently assembled through three SN2 alkynylation reactions a

Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; A novel potent inhibitor of AI-2 signalling

(S)-4,5-Dihydroxypentane-2,3-dione [(S)-DPD, (1)] is a precursor for AI-2, a quorum sensing signalling molecule for inter- and intra-species bacterial communication. The synthesis of its fluoro-analogue, 4-fluoro-5-hydroxypentane- 2,3-dione (2) is reported. An intermediate in this route also enables a new, shorter synthesis of the native (S)-DPD. 4-Fluoro-DPD (2) completely inhibited bioluminescence and bacterial growth of Vibrio harveyi BB170 strain at 12.5 μM and 100 μM, respectively.

A reductive coupling strategy towards ripostatin A

Synthetic studies on the antibiotic natural product ripostatin A have been carried out with the aim to construct the C9-C10 bond by a nickel(0)-catalyzed coupling reaction of an enyne and an epoxide, followed by rearrangement of the resulting dienylcyclopropane intermediate to afford the skipped 1,4,7-triene. A cyclopropyl enyne fragment corresponding to C1-C9 has been synthesized in high yield and demonstrated to be a competent substrate for the nickel(0)-catalyzed coupling with a model epoxide. Several synthetic approaches toward the C10-C26 epoxide have been pursued. The C13 stereocenter can be set by allylation and reductive decyanation of a cyanohydrin acetonide. A mild, fluoride-promoted decarboxylation enables construction of the C15-C16 bond by an aldol reaction. The product of this transformation is of the correct oxidation state and potentially three steps removed from the targeted epoxide fragment.

Synthetic studies toward the C5-C20 domain of the azaspiracids.

[structure: see text]. An approach toward the C5-C20 THF-fused trioxadispiroketal portion of the azaspiracids is reported. The highly substituted azaspiracid D ring (C16-C19) was prepared by the one-pot conversion of a tetraol into a tetrahydrofuran. Effo