950838-18-3

Upstream product

• 98-80-6 phenylboronic acid 
• 67279-69-0 trans-4,5-dihydro-5-iodomethyl-4-phenyl-2(3H)-furanone 
• 5703-57-1 3-phenylpent-4-enoic acid 
• 104-54-1 3-Phenylpropenol 
• 112837-17-9 (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one 
• 906098-15-5 methyl (3S,4R,5R,6S)-3-phenyl-4,5,6-tris(methoxymethoxy)-7-octenoate 
• 906098-14-4 methyl (2E,4R,5R,6S)-4,5,6-tris(methoxymethoxy)-2,7-octadienoate 
• 906098-18-8 (4S,5R)-4,5-dihydro-5-((1R,2S)-1,2-dihydroxybut-3-enyl)-4-phenyl-2(3H)-furanone 
• 81703-93-7 methyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 
• 81703-94-8 methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 
• 357675-06-0 methyl (R)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropanoate 

Relevant academic research and scientific papers

Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: A formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(iii)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.

Stereoselective rhodium-catalyzed conjugate addition of boronic acids to unprotected δ-hydroxy-γ-butenolides. Synthesis of (-)-7-oxamuricatacin and β-substituted derivatives

(Chemical Equation Presented) The chiral δ-hydroxy-γ-butanolide moiety is widely found among biologically active natural products. We report herein the stereoselective synthesis of β-substituted analogues of these compounds by the Rh1-catalyzed

Stereoselective conjugate addition of aryl- And alkenylboronic acids to acyclic γ,δ-oxygen-substituted α,β-enoates

The substrate-controlled Rh1-catalyzed conjugate addition of aryl- and alkenylboronic acids to α,β-unsaturated esters which bear γ- and δ-oxygen substituents takes place in a highly anti diastereoselective fashion either when using γ-hydroxyl u

Synthesis and biological evaluation of aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F structurally related to the amaryllidaceae anticancer constituents

Pancratistatin is a potent anticancer natural product, whose clinical evaluation is hampered by the limited natural abundance and the stereochemically complex structure undermining practical chemical preparation. Fifteen aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F that possess four of the six pancratistatin stereocenters have been synthesized and evaluated for anticancer activity. These compounds serve as truncated pancratistatin analogues lacking the lactam ring B, but retaining the crucial C10a-C10b bond with the correct stereochemistry. The lack of activity of these compounds provides further insight into pancratistatin's minimum structural requirements for cytotoxicity, particularly the criticality of the intact phenanthridone skeleton. Significantly, these series provide rare examples of simple aromatic conduritol and inositol analogues and, therefore, this study expands the chemistry and biology of these important classes of compounds.