203243-30-5

Upstream product

• 100-52-7 benzaldehyde 
• 1150312-99-4 C₁₄H₁₈O₃ 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 53167-11-6 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 
• 245441-88-7 1-[2,2-dimethyl-(6S)-O-(S-methyl dithiocarbonyl)-(3aR,5R,6aR)perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethyl-(1RS)-O-(S-methyl dithiocarbonate) 
• 321868-67-1 2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-(6S)-yl-O-(S-methyl dithicarbonate) 
• 245441-89-8 2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxole 
• 18439-39-9 2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]-dioxol-(6S)-ol 
• 245441-87-6 1,2-O-isopropylidene-5-C-phenyl-β-L-ido/α-D-gluco-pentofuranose 
• 955951-04-9 (S)-ethyl 4-hydroxy-5-phenylpentanoate 
• 955951-03-8 (R)-ethyl 4-anilinoxy-5-phenylpent-2-enoate 
• 104-53-0 3-phenyl-propionaldehyde 
• 415902-37-3 (S)-5-benzyl-dihydrofuran-2(3H)-one 
• 122332-14-3 (S)-1-phenylpent-4-en-2-ol 

Downstream Products

• 321868-56-8 3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5R)-tetrahydrofuran-2-one 

Relevant academic research and scientific papers

Stereocontrolled Synthesis of Harzialactone A and Its Three Stereoisomers by Use of Standardized Polyketide Building Blocks

In this paper, we present a short and convenient synthesis of the natural product Harzialactone A and its three stereoisomers. In a three-step synthesis starting from cheap and commercially available benzaldehyde, we created the small polyketidic compound with full control over its two stereogenic centers. To this end, we employed a chiral building block previously described by us, introducing the first stereogenic center through a Horner–Wittig reaction. The second stereogenic center was installed via stereocontrolled syn- or anti-reduction with the corresponding β-hydroxy ketone intermediates. Upon ozonolysis followed by oxidation the natural product and its stereovariants were produced with excellent enantio- and diastereopurities.

Stereoselective synthesis of cytotoxic marine metabolite harzialactone a by three different routes

The cytotoxic marine metabolite harzialactone A has been synthesized stereoselectively starting from phenylacetaldehyde through three different routes. The key steps were: in the first approach Sharpless asymmetric dihydroxylation, in the second approach

New synthesis of harzialactone A via kinetic resolution using recombinant Fusarium proliferatum lactonase

A new synthesis of harzialactone A together with its stereoisomers was achieved starting from phenyl acetone. The key step of this new route is the kinetic bioresolution of racemic cis- and trans-isomers by recombinant Escherichia coli JM109 cells expressing Fusarium proliferatum lactonase gene (reFPL). Harzialactone A was isolated in excellent ee (>99%), while moderate to good enantioselectivities (80% to >99% ee) were obtained for its isomers.

Synthesis of (3R,5R)-harzialactone a and its (3R,5S)-isomer

The total synthesis of (3R,5R)-harzialactone A (1) and its (3R,5S)-isomer (2) is described. Epoxide opening with thioacetal and diastereoselective reductions are used as key reactions.

Chemoenzymatic asymmetric synthesis of harzia lactone A stereomers

A facile chemoenzymatic synthesis of the harzia lactone A enantiomers was developed. A lipase-catalyzed acylation and an enantio-controlled substrate and reagent-controlled Sharpless' asymmetric dihydroxylation are the key features of the synthesis.

A short synthesis of (+)-harzialactone A and (R)-(+)-4-hexanolide via proline-catalyzed sequential α-aminooxylation and Horner-Wadsworth-Emmons olefination of aldehydes

An efficient and short enantioselective synthesis of the antitumor marine metabolite, (+)-harzialactone A 1 and pheromone, (R)-(+)-4-hexanolide 2 using l-proline-catalyzed sequential α-aminooxylation and Horner-Wadsworth-Emmons olefination of the respecti

Synthesis of harzialactone A and its isomers from D-glucose and assignment of absolute stereochemistry

The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned un

A concise synthesis of harzialactone A from D-glucose and revision of absolute stereochemistry

Synthesis of 2 by a chiron approach is described starting from monoacetone-D-glucose 4. Absolute stereochemistry of natural harzialactone A 1 (2S,4S) is revised to 2 (2R,4R).