55514-49-3

Upstream product

• 5837-78-5 Ethyl tiglate 
• 90177-85-8 4-hydroxy-2-methylbut-2-enoic acid ethyl ester 
• 88865-33-2 ethyl (E)-4-(4-methoxyphenoxy)-2-methyl-2-butenoate 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 80-59-1 Tiglic acid 
• 50471-46-0 ethyl 2-methyl-2-hydroxy-3-butenoate 
• 30018-16-7 (1-ethoxycarbonylethyl)triphenylphosphonium bromide 
• 535-11-5 Ethyl 2-bromopropionate 
• 1647-12-7 ethyl 2-methyl-but-3-enoate 

Downstream Products

• 88865-33-2 ethyl (E)-4-(4-methoxyphenoxy)-2-methyl-2-butenoate 
• 1028267-09-5 6-benzyloxy-6-(5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methyl-hexa-2,4-dienal 
• 936819-05-5 6-benzyloxy-6-(5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methyl-hexa-2,4-dien-1-ol 
• 936819-04-4 6-benzyloxy-6-(5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methyl-hexa-2,4-dienoic acid ethyl ester 
• 1027023-55-7 8-benzyloxy-8-(5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-butyl-4-methyl-octa-1,4,6-trien-3-ol 
• 88865-35-4 (E)-4-(4-methoxyphenoxy)-2-methyl-2-butenal 
• 88865-39-8 2,2-dimethyl-5-<(E)-3-(4-methoxyphenoxy)-1-methyl-1-propenyl>-3(2H)-furanone 
• 78957-33-2 (E)-2,6-dimethyl-8-(4-methoxyphenoxy)-6-octen-3-yne-2,5-diol 
• 78957-40-1 3-acetoxy-2,2-dimethyl-5-<(E)-3-(4-methoxyphenoxy)-1-methyl-1-propenyl>-2,5-dihydrofuran 
• 88865-36-5 (E)-5-acetoxy-2,6-dimethyl-8-(4-methoxyphenoxy)-6-octen-3-yn-2-ol 
• 88865-34-3 (E)-4-(4-methoxyphenoxy)-2-methyl-2-buten-1-ol 
• 223405-97-8 2-methyl-4-(triphenyl-phosphanyl)-but-2-enoic acid ethyl ester bromide salt 

Relevant academic research and scientific papers

Twelve-Step Asymmetric Synthesis of (-)-Nodulisporic Acid C

A short, enantioselective synthesis of (-)-nodulisporic acid C is described. The route features two highly diastereoselective polycyclizations en route to the terpenoid core and the indenopyran fragment and a highly convergent assembly of a challenging indole moiety. Application of this chemistry allows for a 12-step synthesis of the target indoloterpenoid from commercially available material.

4 - Halogenated -2 - methyl -2 - butenoic acid ethyl ester and preparation method thereof

The invention discloses 4 - halogenated -2 - methyl -2 - butenoic acid ethyl ester and a preparation method thereof, and particularly relates to the technical field of chemical intermediate synthesis. The 4 -halogenated -2 -methyl -2 - butenoic acid ethyl ester comprises the following steps: 2 - methyl -3 - butenoic acid ethyl ester is oxidized to synthesize 2 - methyl -2 -hydroxy -3 -butenoic acid ethyl ester. The 2 -methyl -2 -hydroxy -3 -butenoic acid ethyl ester is halogenated to give 4 -halo -2 - methyl -2 -butenoic acid ethyl ester. The synthesis method is simple, the yield is high, the use of toxic liquid bromine and hydrocyanic acid is avoided, and industrial production is easy.

Asymmetric synthesis of α,β-substituted γ-amino acids via conjugate addition

The first conjugate addition reaction of organocuprates to N-enoyl oxazolidinone where a N-protected γ-nitrogen atom and an α-methyl group are present into α, β-unsaturated system is described. This reaction gave anti-products in moderate yields and high diastereomeric ratios. The anti-products have two contiguous stereogenic centers, one formed by the conjugate addition reaction and the other by a diastereoselective protonation reaction. The removal of chiral oxazolidinone moiety and N-deprotection of amino group furnished chiral α, β-disubstituted γ-amino acids.

Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases

Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C?C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.

Total synthesis of AMF-26, an antitumor agent for inhibition of the golgi system, targeting adp-ribosylation factor 1

An effective method for the total synthesis of 1 (AMF-26), a potentially promising new anticancer drug that disrupts the Golgi system by inhibiting the ADP-ribosylation factor 1 (Arf1) activation, has been developed for the first time. The construction of

Total synthesis of (+)-papulacandin D

A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria.

Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates

A method for synthesizing intermediates for use in the synthesis of carotenoid synthetic intermediates, carotenoid analogs, and/or carotenoid derivatives. The carotenoid analog, derivative, or intermediate may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include methods for synthesizing chemical compounds including an analog or derivative of a carotenoid. Carotenoid analogs or derivatives may include acyclic end groups. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.

Synthesis of the C19-C34 segment of amphidinolide C

The synthesis of the C19-C34 segment of amphidinolide C is described. The key steps include the Mioskowski's Lewis acid catalyzed epoxide opening with the alcohol, ring-closing metathesis, Wittig reaction, and Nozaki-Hiyama-Kishi coupling reaction. Georg

METHODS FOR SYNTHESIS OF CHIRAL INTERMEDIATES OF CAROTENOIDS, CAROTENOID ANALOGS, AND CAROTENOID DERIVATIVES

A method used for synthesizing intermediates for use in the synthesis of carotenoids and carotenoid analogs, and/or carotenoid derivatives. In some embodiments, the invention includes methods for synthesizing optically active intermediates useful for the synthesis of optically active carotenoids.

Total synthesis of (-)-stellettamide B and determination of its absolute stereochemistry.

[figure: see text] The first total synthesis of (-)-stellettamide B has been achieved by a sequence based on amide coupling of the chiral 1-(aminomethyl)-indolizidine fragment, prepared by TiCl4-mediated asymmetric allylation of the tricyclic N-acyl-N,O-a