172296-00-3Relevant articles and documents
Studies toward the synthesis of natural and unnatural dienediynes. Part 2: A practical approach to functionalised cyclopentenones
Caddick,Khan,Frost,Smith,Cheung,Pairaudeau
, p. 8953 - 8958 (2000)
The dienediyne natural products contain a functionalised dihydroxylated cyclopentane motif. A critical evaluation of the methods for the preparation and rearrangements of pyranones to give 4,5-dihydroxylated cyclopentenones is presented. (C) 2000 Elsevier Science Ltd.
Kinetic resolution of 4,5-dihydroxylated cyclopentenones
Etheridge, Zac C.,Caddick, Stephen
, p. 503 - 507 (2004)
An asymmetric synthesis of trans-4,5-dihydroxylated cyclopentenones has been developed. The method involves a lipase-mediated kinetic resolution.
Asymmetric synthesis of trans-4,5-dioxygenated cyclopentenone derivatives by organocatalyzed rearrangement of pyranones and enzymatic dynamic kinetic resolution
Nunes, Jo?o P.M.,Veiros, Luís F.,Vaz, Pedro D.,Afonso, Carlos A.M.,Caddick, Stephen
supporting information; experimental part, p. 2779 - 2787 (2011/05/02)
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.
Asymmetric synthesis of functionalised cyclopentenones via organocatalysed rearrangement and enzymatic resolution of pyranones
Nunes, Jo?o P.M.,Afonso, Carlos A.M.,Caddick, Stephen
experimental part, p. 3706 - 3708 (2009/10/11)
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.
Synthesis and melanin biosynthesis inhibitory activity of (±)-terrein produced by Penicillium sp. 20135
Lee, Sangku,Kim, Won-Gon,Kim, Eungsoo,Ryoo, In-Ja,Lee, Hyeong Kyu,Kim, Jae Nyoung,Jung, Sang-Hun,Yoo, Ick-Dong
, p. 471 - 473 (2007/10/03)
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
Caddick, Stephen,Cheung, Steven,Frost, Lisa M.,Khan, Safraz,Pairaudeau, Garry
, p. 6879 - 6882 (2007/10/03)
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
Caddick,Delisser,Doyle,Khan,Avent,Vile
, p. 2737 - 2754 (2007/10/03)
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.
Stereoselective synthesis of a functionalised bicyclic core of neocarzinostatin and kedarcidin chromophores
Caddick, Stephen,Delisser, Vern M.
, p. 2355 - 2358 (2007/10/03)
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.
Preparation of the A-ring of neocarxzinostatin and kedarcidin chromophores via a stereocontrolled base mediated isomerisation reaction
Caddick,Khan
, p. 1971 - 1972 (2007/10/02)
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
Kolb, Hartmuth C,Hoffmann, Martin R.
, p. 5127 - 5144 (2007/10/02)
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.
