77035-56-4

Upstream product

• 66510-25-6 2-chloro-4-methyl-2H-furan-5-one 
• 22122-36-7 3-methyl-5H-furan-2-one 
• 1679-47-6 3-methyltetrahydro-2-furanone 
• 59488-94-7 2-bromo-4-methyl-2H-furan-5-one 
• 194468-85-4 (3aS,6aS)-3-[1-Hydroxy-meth-(Z)-ylidene]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 
• 205648-32-4 C₂₂H₂₄O₄ 
• 194468-88-7 C₂₂H₂₆O₄ 
• 205815-50-5 (3aS,6aS)-3-[1-((2R,3R,4R)-4-Methyl-5-oxo-3-phenylsulfanyl-tetrahydro-furan-2-yloxy)-meth-(E)-ylidene]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 
• 205815-41-4 (3R,4R,5S)-5-bromo-3-methyl-4-phenylsulfanyl-dihydro-furan-2-one 
• 194468-86-5 Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester 
• 159701-81-2 (3R,4R,5R)-5-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-3-methyl-4-phenylsulfanyl-dihydrofuran-2-one 
• 160080-50-2 (3aS,6R,6aR)-6-iodohexahydro-2H-cyclopenta[b]furan-2-one 
• 120262-99-9 (5S)-5-(l-menthyloxy)-3-methyl-2(5H)-furanone 
• 120262-98-8 (5R)-5-(l-menthyloxy)-3-methyl-2(5H)-furanone 

Relevant academic research and scientific papers

Use of Winterfeldt's template to control the C-2' configuration in the synthesis of strigol-type compounds

A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues.

Attempted stereocontrol at C-2' of strigol-type compounds by a Michael reaction/elimination approach

By a Michael addition/nucleophilic substitution/elimination sequence the stereocontrol at C-2' in strigol-typed compounds is in principle possible. However, the method is unsuitable for practical application since it has been shown that a stereolabile intermediate is involved.

Strigol and sorgolactone synthetic studies use of Winferfeldt's template to control the C-2' configuration

A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues.

The Preparation of Synthetic Analogues of Strigol

A range of analogues of the natural germination stimulant, strigol, for parasitic weeds of the genera Striga and Orobanche, has been prepared.Most of the products contain an α-formyl-γ-lactone (or α-formyl-γ-lactam) grouping attached through an enol-ether linkage to the 5-position of a but-2-enolide.Some have shown sufficiently high activities as to warrant large-scale field trials.