126566-41-4

Usage

InChI:InChI=1/C9H14O3/c1-9(2,3)12-7-5-4-6(10)8(7)11/h4-5,7-8,11H,1-3H3/t7-,8-/m0/s1

Upstream product

• 71443-31-7 6-t-butoxy-2,3-dihydro-6H-pyrano-3-one 
• 62644-49-9 6-acetoxy-2H-pyran-3(6H)-one 
• 71443-22-6 1-O-benzoyl-2,3-dideoxy-D,L-pent-2-enopyranos-4-ulose 
• 35436-57-8 6-hydroxy-3,6-dihydro-2H-pyran-3-one 

Downstream Products

• 172296-00-3 (4R,5S)-4-t-butoxy-5-hydroxy-cyclopenten-1-one 
• 172296-00-3 (4S,5R)-4-t-butoxy-5-hydroxy-cyclopenten-1-one 
• 582-46-7 (+/-)-terrein 

Relevant academic research and scientific papers

Asymmetric synthesis of functionalised cyclopentenones via organocatalysed rearrangement and enzymatic resolution of pyranones

A direct asymmetric synthesis of a trans-4,5-difunctionalised cyclopentenone derivative has been achieved in 55% yield and 80% ee by organocatalysed rearrangement of a pyranone in tert-butanol by DABCO with simultaneous enzymatic resolution.

Stereoselective synthesis of a functionalised bicyclic core of neocarzinostatin and kedarcidin chromophores

The stereoselective synthesis of a bicyclic ring system related to Neocarzinostatin and Kedarcidin Chromophores is described; key steps involve stereoselective conjugate addition of an enediyne to an enone and intramolecular aldol reaction of a cobalt complexed alkynyl aldehyde.

Asymmetric synthesis of trans-4,5-dioxygenated cyclopentenone derivatives by organocatalyzed rearrangement of pyranones and enzymatic dynamic kinetic resolution

Dioxygenated cyclopentenones are versatile building blocks for the synthesis of several natural products. Herein we report a direct asymmetric synthesis of trans-4,5-dioxygenated cyclopentenone derivatives through base-catalyzed rearrangement of pyranones followed by dynamic kinetic resolution. Milder conditions than previously reported for this rearrangement have been found regarding amine base catalysis, solvent and temperature effects. All data supports a mechanism involving cyclization of an intermediate formed by electrocyclic ring opening of a pyranone-derived enol. We have developed conditions for asymmetric synthesis of trans-4-tert-butoxy-5-hydroxycyclopent-2- enone, in 81% yield and 95% ee, and analogous dioxygenated cyclopentenones, via a lipase induced dynamic kinetic resolution.

Synthesis and melanin biosynthesis inhibitory activity of (±)-terrein produced by Penicillium sp. 20135

Terrein was isolated from Penicillium sp. 20135, prepared by a practical synthetic way, and evaluated first time for its melanin biosynthesis inhibitory activity. Terrein was isolated from Penicillium sp. 20135, prepared by a practical synthetic way, and evaluated first time for its melanin biosynthesis inhibitory activity.

Synthesis of functionalised cyclopentenones via rearrangement of pyranones

Substituted functionalised cyclopentenones could be obtained via base-mediated isomerisation of pyranones. (C) 2000 Elsevier Science Ltd.

Studies toward the synthesis of natural and unnatural dienediynes 1. Approaches to a functionalised bicyclic ring system

The synthesis of a functionalised bicyclic ring system related to the naturally occurring dienediynes, NCS and Kedarcidin Chromophores is presented. Key steps involve: conjugate addition of an enediyne to a functionalized enone and intramolecular boron mediated aldol reaction.

Preparation of the A-ring of neocarxzinostatin and kedarcidin chromophores via a stereocontrolled base mediated isomerisation reaction

A new base promoted isomerisation of 6-(1,1-dimethylethoxy)-2H-pyran-3-one to 4-(1,1-dimethylethoxy)5-hydroxy-2-cyclopentenone is used in the preparation of 2-bromo-5-[(1,1-dimethylethyl)dimethylsilyloxy]4-hydroxy-2-cyclopentenone, a potential intermediat

A RING CONTRACTION OF 6-ALKOXY-2,3-DIHYDRO-6H-PYRAN-3-ONES TO POLYFUNCTIONALIZED CYCOPENTENONES

The rearrangement of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (1) to trans-4-alkoxy-5-hydroxy-2-cyclopenten-1-ones (2) has been optimized.The effect of buffer concentration (PhCO2H/KOAc) on reaction rate and yield suggests specific acid catalysis.Substitution patterns and influence of the 6-alkoxy substituent have been investigated.Applications in natural product synthesis are described.

IMPROVED PROCEDURE FOR THE SYNTHESIS OF 6-ALKOXY-2,3-DIHYDRO-6H-PYRAN-3-ONES (2,3-DIDEOXY-DL-PENT-2-ENOPYRANOS-4-ULOSES). NEAT CONVERSION INTO POLYFUNCTIONALIZED CYCLOPENTENONES.

The glycosidic bond of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (3) is made advantageously in the presence of catalytic ZnCl2*etherate.A palladium-assisted transformation of 3 affords trans-4-alkoxy-5-hydroxy-2-cyclopenten-1-ones (4) in good yield.