274258-70-7

Upstream product

• 67-56-1 methanol 
• 141-82-2 malonic acid 
• 5470-84-8 4-benzyloxybutanal 
• 100-39-0 benzyl bromide 
• 16695-14-0 Malonic acid monomethyl ester 
• 4541-14-4 4-benzyloxy-butan-1-ol 
• 3724-55-8 methyl but-3-enoate 
• 70388-33-9 4-benzyloxybut-1-ene 

Downstream Products

• 865872-24-8 (4S,5S)-5-(2-benzyloxyethyl)-4-hydroxydihydrofuran-2(3H)-one 
• 274258-71-8 (4R,5R)-5-(2-benzyloxyethyl)-4-hydroxydihydrofuran-2-one 
• 329010-34-6 (4S)-4-[(2R,4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(5-trimethylsilanylpent-2-(E)-en-4-ynyl)tetrahydrofuran-2-yl]-2,2-dimethyl-[1,3]dioxolane 
• 329010-30-2 (2S)-1-[(2R,4R,5R)-5-(2-benzyloxyethyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydrofuran-2-yl]-ethane-1,2-diol 
• 329010-33-5 (2R,4R,5R)-[2-(2-benzyloxyethyl)-5-(2,2-dimethyl-[1,3]dioxolan-4(S)-4-yl)-tetrahydrofuran-3-yloxy]-tert-butyldiphenylsilane 
• 329010-31-3 ethyl (2E)(5R,6R)-8-benzyloxy-5-(tert-butyldiphenylsilanyloxy)-6-hydroxyoct-2-enoate 
• 329010-32-4 (2E)(5R,6R)-8-benzyloxy-5-(tert-butyldiphenylsilanyloxy)-oct-2-ene-1,6-diol 
• 329010-26-6 (4R,5R)-5-(2-benzyloxyethyl)-4-(tert-butyldiphenylsilanyloxy)dihydrofuran-2-one 
• 329010-28-8 (4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one 
• 329010-27-7 (4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(2-hydroxyethyl)-dihydrofuran-2-one 

Relevant academic research and scientific papers

A short synthesis of trans-(+)-laurediol

A highly convergent and short synthesis of trans-(+)-laurediol is presented. The synthesis features a highly efficient construction of a cis-3- hydroxy-γ-butyrolactone through a Sharpless AD reaction of a β,γ- unsaturated ester. (C) 2000 Elsevier Science Ltd.

Toward the synthesis of spirastrellolide A: Construction of a tetracyclic C26-C40 subunit containing the DEF-bis-spiroacetal

(Chemical Equation Presented) A stereocontrolled synthesis of the fully elaborated C26-C40 tricyclic [5,6,6]-bis-spiroacetal of spirastrellolide A containing the C28 chlorine substituent is reported, exploiting asymmetric

A Catalytic Asymmetric Protecting-Group-Free Total Synthesis of (4 S,5 S)-4,8-Dihydroxy-3,4-dihydrovernoniyne and Its Enantiomer

A catalytic asymmetric second generation synthesis of (4S,5S)-4,8-dihydroxy-3,4-dihydrovernoniyne has been completed employing the asymmetric dihydroxylation strategy. Further, a four-step protecting-group-free synthesis of the natural product and its enantiomer has been achieved through the modified Knoevenagel reaction, asymmetric dihydroxylation, and Cadiot-Chodkiewicz coupling. The protecting-group-free synthesis is completed in four steps and 41% overall yield.

Synthesis of the DEF-bis-spiroacetal of spirastrellolide a exploiting a double asymmetric dihydroxylation/spiroacetalisation strategy

An efficient synthesis of the C26-C40 tricyclic [5,6,6]-bis-spiroacetal segment of the marine macrolide spirastrellolide A has been developed, exploiting a novel double Sharpless asymmetric dihydroxylation/spiroacetalisation sequence. The Royal Society of Chemistry 2006.

β-hydroxy-γ-lactones as chiral building blocks for the enantioselective synthesis of marine natural products

The enantioselective synthesis of trans-(+)-laurediol, (2S,3S,5R)-5-[(1R)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol, and (2S,3S,5S)-5-[(1S)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol are described. In addition, a formal synthesis of trans-(-)-kumausyne is also developed. All the synthetic procedures have in common the use of enantiomerically enriched β-hydroxy-γ-lactones, easily available by Sharpless asymmetric dihydroxylation (AD) from the suitable β,γ-unsaturated ester. The use of Katsuki - Sharpless asymmetric epoxidation (AE) as an additional enantioselective reaction provides cyclic compounds of high enantiomeric purity.