67772-76-3

Usage

InChI:InChI=1/C7H8O4/c8-2-3-1-4(9)6-7(11-6)5(3)10/h1,4,6-9H,2H2/t4-,6+,7-/m0/s1

Upstream product

• 76596-36-6 Chloro-acetic acid (1S,2R,3S,4S,6R)-3-bromo-4-(2-chloro-acetoxymethyl)-5-oxo-7-oxa-bicyclo[4.1.0]hept-2-yl ester 
• 792910-35-1 Acetic acid (1R,2S,6R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-2-yl ester 
• 532989-49-4 (2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxycyclohexan-1-one 
• 455330-48-0 (1R,2S)-2-acetoxy-5,5-ethylenedioxycyclohexane carboxylic acid 
• 455330-49-1 (1S)-4,4-ethylenedioxy-2-iodo-1-cyclohexyl acetate 
• 532989-56-3 Acetic acid (S)-(1,4-dioxa-spiro[4.5]dec-6-en-8-yl) ester 
• 455330-50-4 (1S)-4,4-ethylenedioxy-2-cyclohexen-1-ol 
• 96893-99-1 (1R,2S)-5,5-(Ethylendioxy)-2-hydroxycyclohexancarbonsaeure-ethylester 
• 119478-74-9 (S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enone 
• 792910-34-0 C₂₀H₃₀O₅Si 
• 2435-32-7 6,7-epoxy-1,4,4a,6,7,8a-hexahydro-1,4-methano-naphthalene-5,8-dione 
• 792910-36-2 (1R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxy-7-oxa-bicyclo[4.1.0]hept-3-en-2-one 
• 174156-50-4 (2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-hydroxymethyl-5-cyclohexen-1-one 

Downstream Products

• 76596-39-9 (4R,5S,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-propylsulfanyl-cyclohex-2-enone 
• 27270-89-9 (5S,6R)-5,6-epoxy-2-hydroxymethylcyclohex-2-ene-1,4-dione 

Relevant academic research and scientific papers

Enantioselective total synthesis of epoxyquinone natural products (-)-phyllostine, (+)-epoxydon, (+)-epiepoxydon and (-)-panepophenanthrin: Access to versatile chiral building blocks through enzymatic kinetic resolution

A new enzyme mediated protocol to access versatile chiral building blocks for the synthesis of epoxyquinone natural products is delineated. Total syntheses of (-)-phyllostine, (+)-epoxydon, (+)-epiepoxydon and (-)-panepophenanthrin have been accomplished to demonstrate the efficacy of this approach.

Total synthesis of (+)-epiepoformin, (+)-epiepoxydon and (+)-bromoxone employing a useful chiral building block, ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanecarboxylate

Enantioselective total synthesis of (+)-epiepoformin 1, (+)-epiepoxydon 2 and (+)-bromoxone 3 using a chiral building block, ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclo- hexanecarboxylate 6, is described. Since the synthesis afforded intermediates 18, 2 and 25, it accomplished a formal synthesis of (-)-theobroxide 19, (-)-phyllostine 22, (+)-herveynone 27 and (-)-asperpentyn 28. The usefulness of 6 for the synthesis of natural epoxycyclohexene derivatives was demonstrated.

The synthesis of epi-epoxydon utilising the Baylis-Hillman reaction

(±)-epi-Epoxydon was synthesised by means of a triethylaluminium/tri-n-butylphosphine-catalysed Baylis-Hillman reaction between an O-protected epoxidised hydroxyquinol core and paraformaldehyde, constituting the first application of the Baylis-Hillman reaction to a highly functionalised β-substituted enone.

Stereo- and enantio-controlled synthesis of two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (-)-phyllostine, via catalytic asymmetrization of a meso substrate

Two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (-)-phyllostine, have been first synthesized in stereo- and enantio-controlled manner using a chiral cyclohexadienol synthon prepared by catalytic asymmetrization of a meso substrate. The synthesis has verified the proposed absolute structures of these natural products which have been deduced by CD measurements.