219610-75-0

Upstream product

• 14593-43-2 benzyl allyl ether 
• 2386-64-3 ethylmagnesium chloride 
• 3587-60-8 Benzyloxymethyl chloride 
• 163457-34-9 (+)-(4S)-3-<(2'R)-2'-((benzyloxy)methyl)butanoyl>-4-benzyl-2-oxazolidinone 

Downstream Products

• 916501-76-3 (S)-(2-ethylhex-3-enyloxymethyl)benzene 
• 916501-82-1 (4S,4'R,6R)-4,6-diethyl-4-(4-ethyl-2-methyloct-1-enyl)-2-phenyl-6-vinyl-1,3-dioxane 
• 916501-80-9 (4S,4'R,6R)-4,6-diethyl-4-(4-ethyl-2-methylocta-1,5-dienyl)-2-phenyl-6-vinyl-1,3-dioxane 
• 916501-87-6 (4S,4'R,6S)-4,6-diethyl-4-(4-ethyl-2-methylocta-1,5-dienyl)-2-phenyl-6-vinyl-1,3-dioxane 
• 1653-16-3 (S)-3-iodomethylheptane 
• 1643478-23-2 (R)-4-((4-methoxybenzyloxy)methyl)hexan-3-one 
• 1312543-69-3 C₃₄H₆₄O₄Si₂ 
• 1312543-70-6 (3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol 
• 1312543-57-9 C₂₈H₄₈O₄Si 
• 1643478-33-4 C₃₅H₆₄O₆S₂Si₂ 
• 1643478-27-6 (3R,5R,6R,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecan-4-one 
• 1643478-40-3 C₃₃H₆₂O₅Si₂ 
• 1643478-29-8 (3R,4S,5S,6S,7R,8S)-8,10-bis(tert-butyldimethylsilyloxy)-3-((4-methoxybenzyloxy)methyl)-5,7-dimethyldecane-4,6-diol 
• 1643478-64-1 (1E,3E,7S,8R,10R,11R,12R)-7-(tert-butyldimethylsilyloxy)-1-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-12-ethyl-11-hydroxy-8,10-dimethyltetradeca-1,3,13-trien-5-one 

Relevant academic research and scientific papers

Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C-H Functionalization

Polyketide synthases (PKSs) represent a powerful catalytic platform capable of effecting multiple carbon-carbon bond forming reactions and oxidation state adjustments. We explored the functionality of two terminal PKS modules that produce the 16-membered tylosin macrocycle, using them as biocatalysts in the chemoenzymatic synthesis of tylactone and its subsequent elaboration to complete the first total synthesis of the juvenimicin, M-4365, and rosamicin classes of macrolide antibiotics via late-stage diversification. Synthetic chemistry was employed to generate the tylactone hexaketide chain elongation intermediate that was accepted by the juvenimicin (Juv) ketosynthase of the penultimate JuvEIV PKS module. The hexaketide is processed through two complete modules (JuvEIV and JuvEV) in vitro, which catalyze elongation and functionalization of two ketide units followed by cyclization of the resulting octaketide into tylactone. After macrolactonization, a combination of in vivo glycosylation, selective in vitro cytochrome P450-mediated oxidation, and chemical oxidation was used to complete the scalable construction of a series of macrolide natural products in as few as 15 linear steps (21 total) with an overall yield of 4.6%.

Synthetic studies of microtubule stabilizing agent peloruside A: An asymmetric synthesis of C10-C24 segment

An asymmetric synthesis of the C10-C24 fragment of the potent antitumor macrolide, peloruside A is described. All three stereogenic centers have been enantioselectively constructed utilizing Evans alkylation, Brown asymmetric allylboration, and a substrate controlled epoxide formation. Other key reactions involved Grubbs's ring-closing olefin metathesis and Ando's Z-selective olefination reaction.

Asymmetric ethylmagnesiation of alkenes using a novel zirconium catalyst

The novel C1-symmetric zirconocene CpCp°ZrCl2 (Cp=C5h5, Cp°= 1- neomenthyl-4, 5, 6, 7-tetrahydroindenyl) is a cheap, active, and effective catalyst for the asymmetric ethylmagnesiation of unactivated terminal alkenes.

Total Synthesis of Myxovirescins, 2. Assembly of the "Northwestern" Part

The part of the target molecules myxovirescins A and M containing the atoms C(15)-C(28) is described in this paper (for retrosynthetic analysis see Scheme 1).There are three stereogenic centers which are incorporated by using (S)-2-hydroxymethyl-butanoic acid and the appropriate enantiopure diastereoisomeric 2,4-dimethyl-glutaric acids as building blocks (Schemes 2-4).These are joined by the achiral unit 4-oxo-hex-5-enoic acid.The key steps of the assembly are a cuprate Michael addition (Scheme 5) and a nucleophilic addition of a Li derivative to an aldehyde (Scheme 6).In both cases the organometallic reagents are generated by I/Li exchange using two equiv. of tBuLi.The chiral building blocks are prepared by yeast reduction of ethyl 2-formyl-butanoate and by resolution of the 2,4-dimethyl-pentanedioic acid monomethyl ester with phenethylamine; both enantiomers derived from the meso-2,4-dimethyl-glutaric acid are converted to the same aldehyde (5a; "meso-trick", Schemes 3 and 4).The "northwestern" parts for the final synthesis are actually hydroxy sulfones (2 in Scheme 6), the termini of which are ready for Julia coupling and oxidation to a carboxylic acid group.The preparation of the intermediates on gram scales is described and all new compounds are fully characterized by their physical properties, by spectroscopy (IR, 1H- and 13C-NMR spectra) and by elemental analysis. - Key Words: Myxovirescins / Myxococcus virescens / Antibiotics / Macrolides / Lactones / Lactams / Iodine-lithium exchange / Michael additions