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Paul A. Clarke

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Organization: University of York
Department: Department of Chemistry
Title:
Diastereoselective synthesis of functionalized 2-methyltetrahydropyran-4-ones
Co-reporter:Paul A. Clarke, Philip B. Sellars, Nimesh Mistry
Tetrahedron Letters 2011 Volume 52(Issue 28) pp:3654-3656
Publication Date(Web):13 July 2011
DOI:10.1016/j.tetlet.2011.05.022
A simple procedure for the synthesis of functionalized 2-methyl-2,3-dihydropyran-4-ones, based on the Maitland–Japp reaction, and their diastereoselective conversion into functionalized 2-methyltetrahydropyran-4-ones has been developed. This allows access to a structural unit present in a large number of biologically active natural products, and has been successfully applied to the synthesis of the molecule found in Civet cat secretion.
Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions
Co-reporter:Laurence Burroughs, Matthew E. Vale, James A. R. Gilks, Henrietta Forintos, Christopher J. Hayes and Paul A. Clarke  
Chemical Communications 2010 vol. 46(Issue 26) pp:4776-4778
Publication Date(Web):20 May 2010
DOI:10.1039/C0CC00613K
Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under aqueous conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of (L)-proline yield (L)-carbohydrates, esters of (L)-leucine and (L)-alanine generate (D)-carbohydrates, offering the potential to account for the prebiotic link between natural (L)-amino acids and natural (D)-sugars.
Synthetic studies on the phorboxazoles: a short synthesis of an epi-C23 tetrahydropyran core
Co-reporter:Paul A. Clarke, Jason M. Hargreaves, Daniel J. Woollaston, Rosa María Rodríguez Sarmiento
Tetrahedron Letters 2010 Volume 51(Issue 36) pp:4731-4733
Publication Date(Web):8 September 2010
DOI:10.1016/j.tetlet.2010.07.012
Studies on the synthesis of the anticancer natural products, the phorboxazoles have led to the synthesis of the C21–C32 penta-substituted tetrahydropyran core which is epimeric to the natural product at C23. The synthesis was achieved in only seven linear steps. The key steps were the use of a Masamune–Abiko anti-aldol reaction, the formation of a dihydropyran precursor molecule by the use of a new ‘Maitland–Japp-like’ cyclisation, and a highly diastereoselective reductive alkylation of the dihydropyran double bond, to generate the corresponding tetrahydropyran ring in an excellent yield.
Combining pot, atom and step economy (PASE) in organic synthesis. Synthesis of tetrahydropyran-4-ones
Co-reporter:Paul A. Clarke, Soraia Santos and William H. C. Martin  
Green Chemistry 2007 vol. 9(Issue 5) pp:438-440
Publication Date(Web):27 Feb 2007
DOI:10.1039/B700923B
The combination of pot, atom and step economy (PASE) in the synthesis of organic molecules of medium complexity can lead to a significant ‘greening’ of a synthetic route. This is demonstrated by the synthesis of highly substituted tetrahydropyran-4-ones and is quantified by a series of recognised metrics, which demonstrate the efficiency of combining PASE over conventional synthetic strategies.
Strategies for the Formation of Tetrahydropyran Rings in the Synthesis of Natural Products
Co-reporter:Paul A. Clarke;Soraia Santos
European Journal of Organic Chemistry 2006 Volume 2006(Issue 9) pp:
Publication Date(Web):9 FEB 2006
DOI:10.1002/ejoc.200500964

This microreview surveys the literature over the last five years with regard to construction of functionalised tetrahydropyran (THP) rings in the context of the synthesis of natural products. The overview given is intended to provide a working knowledge of the area for those who are unfamiliar, and to refresh and remind those who do work in the area of the exciting developments in the field. While the construction of the THP rings in a number of natural products has been reviewed, we have attempted to highlight the different strategies by focusing on two natural products, namely phorboxazole and centrolobine as case studies. Over the last five years, these natural products have become a test bed for new methods for the construction of THP rings. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions
Co-reporter:Laurence Burroughs, Matthew E. Vale, James A. R. Gilks, Henrietta Forintos, Christopher J. Hayes and Paul A. Clarke
Chemical Communications 2010 - vol. 46(Issue 26) pp:NaN4778-4778
Publication Date(Web):2010/05/20
DOI:10.1039/C0CC00613K
Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under aqueous conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of (L)-proline yield (L)-carbohydrates, esters of (L)-leucine and (L)-alanine generate (D)-carbohydrates, offering the potential to account for the prebiotic link between natural (L)-amino acids and natural (D)-sugars.
CAS:1314789-30-4
1-Pyrrolidinecarboxylic acid, 2-[(R)-hydroxyphenylmethyl]-,1,1-dimethylethyl ester, (2R)-
1-Pyrrolidinecarboxylic acid, 2-[(R)-hydroxyphenylmethyl]-,1,1-dimethylethyl ester, (2R)-
CAS:913642-88-3
1-Pyrrolidinecarboxylic acid, 2-[(R)-hydroxyphenylmethyl]-,1,1-dimethylethyl ester, (2R)-
1-AZETIDINECARBOXYLIC ACID, 2-METHYL-, 1,1-DIMETHYLETHYL ESTER, (2R)-
1-AZETIDINECARBOXYLIC ACID, 2-METHYL-, 1,1-DIMETHYLETHYL ESTER, (2R)-
CAS:791614-70-5
1-AZETIDINECARBOXYLIC ACID, 2-METHYL-, 1,1-DIMETHYLETHYL ESTER, (2R)-
CAS:475301-86-1
1-Azetidinecarboxylic acid, 2-[(methoxymethylamino)carbonyl]-,1,1-dimethylethyl ester, (2S)-
1-Azetidinecarboxylic acid, 2-[(methoxymethylamino)carbonyl]-,1,1-dimethylethyl ester, (2S)-
CAS:327604-82-0
1-Azetidinecarboxylic acid, 2-[(methoxymethylamino)carbonyl]-,1,1-dimethylethyl ester, (2S)-
6-Heptenoic acid, 5-hydroxy-3-oxo-7-phenyl-, methyl ester, (E)-(±)-
6-Heptenoic acid, 5-hydroxy-3-oxo-7-phenyl-, methyl ester, (E)-(±)-
CAS:141928-29-2
6-Heptenoic acid, 5-hydroxy-3-oxo-7-phenyl-, methyl ester, (E)-(±)-
2H-Pyran-2-ethanol, tetrahydro-6-methyl-, cis-
2H-Pyran-2-ethanol, tetrahydro-6-methyl-, cis-
CAS:116500-80-2
2H-Pyran-2-ethanol, tetrahydro-6-methyl-, cis-
6-OCTENOIC ACID, 5-HYDROXY-3-OXO-, METHYL ESTER, (E)-
6-OCTENOIC ACID, 5-HYDROXY-3-OXO-, METHYL ESTER, (E)-
CAS:107400-36-2
6-OCTENOIC ACID, 5-HYDROXY-3-OXO-, METHYL ESTER, (E)-
1-Propanethione,2,2-dimethyl-1-(1-pyrrolidinyl)-
1-Propanethione,2,2-dimethyl-1-(1-pyrrolidinyl)-
CAS:77902-87-5
1-Propanethione,2,2-dimethyl-1-(1-pyrrolidinyl)-
L-Proline, 1-(2,2-dimethyl-1-oxopropyl)-, methyl ester
L-Proline, 1-(2,2-dimethyl-1-oxopropyl)-, methyl ester
CAS:71449-45-1
L-Proline, 1-(2,2-dimethyl-1-oxopropyl)-, methyl ester