24292-29-3

Usage

Uses

Used in Organic Synthesis:
(1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one is used as a building block for the synthesis of more complex molecules. Its unique structure allows for the creation of a variety of compounds with different properties and potential applications.
Used in Medicinal Chemistry:
(1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one is used as a starting material for the development of pharmaceuticals. Its potential biological activities and reactivity make it a valuable component in the design and synthesis of new drugs.
Used in Pharmaceutical Development:
(1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one is used as a component in the development of pharmaceuticals due to its potential therapeutic properties. Its unique structure and reactivity may contribute to the discovery of new drugs with novel mechanisms of action.
Used in Biological Research:
(1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one is used in biological research to explore its potential biological activities. Its bicyclic structure may exhibit interesting interactions with biological systems, providing insights into new therapeutic approaches and applications.

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+/m1/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 
• 55164-61-9 (+/-)-(1α,5α,6α)-5-hydroxy-7-oxabicyclo<4.1.0>hept-3-en-2-one 

Downstream Products

• 32744-80-2 2-chloro-6-(hydroxymethyl)benzene-1,4-diol 
• 76596-39-9 (4R,5S,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-propylsulfanyl-cyclohex-2-enone 

Relevant academic research and scientific papers

Synthesis of (+)-Epoxydon, (–)-Phyllostine, (–)-RKTS 33, and (–)-Parasitenone Featuring Selective Sulfonylation and Oxirane Ring Closure of Aldol Cyclization Products

Two new synthetic approaches to anhydrogabosines are developed from the polyoxygenated aldol cyclization intermediates, bearing different O-protecting groups, which were transformed to various gabosine-type cyclitols. Selective sulfonylation on the required hydroxyl group of the intermediates and the subsequent oxirane ring closure are employed as the key steps in both approaches, by which (+)-epoxydon, (–)-phyllostine, (–)-RKTS 33, and (–)-parasitenone were synthesized from δ-d-gluconolactone.

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.

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.