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Amino acid-catalyzed synthesis of amino acid derivatives: Application and semi-synthesis of Paclitaxel, Docetaxel and their derivatives
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. (Armando Córdova)
2010 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

This thesis deals with different applications of organocatalysis, where amino acid derivatives and small peptides are applied as catalysts. First, the development of environmentally friendly aldol reactions, carried out in aqueous media is illustrated. The corresponding β-hydroxy ketones are formed with ee´s up to 99%. Chapter 3 describes the ability of β3-amino acids to selectively catalyze Mannich-type reactions and govern the formation of products with high anti-selectivity (up to >19:1) and ee´s up to 99%. In the following chapter, an amino acid-catalyzed one-pot three component Mannich reaction between dihydroxyacetone and PMP-protected imines, is presented. The corresponding a,a’-dihydroxy-b-aminoketones are obtained in high yields and with 82-95% ee. Next, an aza-Morita-Baylis-Hillman reaction was investigated where L-proline is the catalyst. The reaction proceeds with excellent chemo- and enantioselectivity to give the corresponding compounds in good yields and with 97-99% ee. Finally, the last part describes development of a proline-catalyzed Mannich reation between N-acyl imines and protected α-hydroxyaldehyes, providing access to different α-hydroxy-β-amino acids in good yields and high enantioselctivity (92-99% ee). The obtained amino acids were further applied in the semisynthesis of paclitaxel and docetaxel derivatives.

Ort, förlag, år, upplaga, sidor
Stockholm: Department of Organic Chemistry, Stockholm University , 2010. , s. 73
Nyckelord [en]
Organocatlysis, amino acids, syntesis, Taxol and Taxotere derivatives
Nationell ämneskategori
Annan medicinsk grundvetenskap
Forskningsämne
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-39138ISBN: 978-91-7447-091-8 (tryckt)OAI: oai:DiVA.org:su-39138DiVA, id: diva2:318680
Disputation
2010-06-11, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16b, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Anmärkning
At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 7: Manuscript.Tillgänglig från: 2010-05-20 Skapad: 2010-05-10 Senast uppdaterad: 2018-01-12Bibliografiskt granskad
Delarbeten
1. The small peptide-catalyzed direct asymmetric aldol reaction in water
Öppna denna publikation i ny flik eller fönster >>The small peptide-catalyzed direct asymmetric aldol reaction in water
2006 (Engelska)Ingår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 4, s. 38-40Artikel i tidskrift (Refereegranskat) Published
Nationell ämneskategori
Annan medicinsk grundvetenskap
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-39047 (URN)10.1039/b515880j (DOI)
Tillgänglig från: 2010-05-06 Skapad: 2010-05-06 Senast uppdaterad: 2018-01-12Bibliografiskt granskad
2. Acyclic beta-amino acid catalyzed asymmetric anti-selective Mannich-type reactions
Öppna denna publikation i ny flik eller fönster >>Acyclic beta-amino acid catalyzed asymmetric anti-selective Mannich-type reactions
2007 (Engelska)Ingår i: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 18, nr 9, s. 1033-1037Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

 The ability of a primary amine containing acyclic beta(3)-amino acids to catalyze direct asymmetric anti-selective Mannich-type reactions is presented. The reactions are generally highly diastereo- and enantioselective to give the corresponding Mannich products with up to >19:1 dr (anti/syn) and 88-99% ee.

Identifikatorer
urn:nbn:se:su:diva-19291 (URN)10.1016/j.tetasy.2007.04.024 (DOI)000247898000001 ()
Tillgänglig från: 2007-11-01 Skapad: 2007-11-01 Senast uppdaterad: 2017-12-13Bibliografiskt granskad
3. Direct catalytic asymmetric three-component Mannich reactions with dihydroxyacetone: enantioselective synthesis of amino sugar derivatives
Öppna denna publikation i ny flik eller fönster >>Direct catalytic asymmetric three-component Mannich reactions with dihydroxyacetone: enantioselective synthesis of amino sugar derivatives
2008 (Engelska)Ingår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 49, nr 5, s. 803-807Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Highly enantioselective, amino acid-catalyzed, one-pot three-component asymmetric Mannich reactions between dihydroxyacetone, p-anisidine, and aldehydes are presented. The reactions proceeded with high chemo- and stereoselectivity and furnished the corresponding α,α′-dihydroxy-β-aminoketones in high yields with 82–95% ee.

Identifikatorer
urn:nbn:se:su:diva-13153 (URN)10.1016/j.tetlet.2007.11.196 (DOI)000253170200014 ()
Tillgänglig från: 2008-12-03 Skapad: 2008-12-03 Senast uppdaterad: 2017-12-13Bibliografiskt granskad
4. Aza-Morita-Baylis-Hillman-type reactions: highly enantioselective organocatalytic addition of unmodified alpha-beta-unsaturated aldehydes to N-Boc protected imines
Öppna denna publikation i ny flik eller fönster >>Aza-Morita-Baylis-Hillman-type reactions: highly enantioselective organocatalytic addition of unmodified alpha-beta-unsaturated aldehydes to N-Boc protected imines
2007 (Engelska)Ingår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 48, nr 39, s. 6900-6904Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Highly enantioselective catalytic routes to Boc protected aza-Morita-Baylis-Hiliman-type products are presented. The organocatalytic asymmetric reactions between unmodified alpha,beta-unsaturated aldehydes and N-Boc protected aryl imines proceed with excellent chemo- and enantioselectivity to give the corresponding compounds in good yields with 97-99% ee

Identifikatorer
urn:nbn:se:su:diva-19364 (URN)10.1016/j.tetlet.2007.07.154 (DOI)000249752500016 ()
Tillgänglig från: 2007-11-07 Skapad: 2007-11-07 Senast uppdaterad: 2017-12-13Bibliografiskt granskad
5. Catalytic asymmetric synthesis of the docetaxel (Taxotere) side chain: organocatalytic highly enantioselective synthesis of esterification-ready alpha-hydroxy-beta-amino acids
Öppna denna publikation i ny flik eller fönster >>Catalytic asymmetric synthesis of the docetaxel (Taxotere) side chain: organocatalytic highly enantioselective synthesis of esterification-ready alpha-hydroxy-beta-amino acids
2008 (Engelska)Ingår i: Tetrahedron Letters, ISSN 0040-4039, Vol. 49, nr 47, s. 6631-6634Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

A highly enantioselective catalytic route to protected β-amino-α-hydroxy acids, such as the side chain of Taxotere, is presented. The organocatalytic asymmetric reactions between unmodified protected α-oxyaldehydes and N-Boc-protected aryl imines give the corresponding compound with up to >19:1 dr and 99–99% ee.

Identifikatorer
urn:nbn:se:su:diva-15773 (URN)10.1016/j.tetlet.2008.09.038 (DOI)000260944900008 ()
Tillgänglig från: 2008-12-10 Skapad: 2008-12-10 Senast uppdaterad: 2010-05-12Bibliografiskt granskad
6. Highly enantioselective organocatalytic addition of aldehydes to N-(phenylmethylene)benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues
Öppna denna publikation i ny flik eller fönster >>Highly enantioselective organocatalytic addition of aldehydes to N-(phenylmethylene)benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues
2009 (Engelska)Ingår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, nr 16, s. 4044-4048Artikel i tidskrift (Refereegranskat) Published
Ort, förlag, år, upplaga, sidor
Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA, 2009
Nyckelord
aldehydes, asymmetric catalysis, (phenylmethylene)benzamides, organocatalysis, taxol
Nationell ämneskategori
Kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-28211 (URN)10.1002/chem.200900078 (DOI)000265509700013 ()
Tillgänglig från: 2009-06-10 Skapad: 2009-06-10 Senast uppdaterad: 2017-12-13Bibliografiskt granskad
7. Practical amino acid-catalyzed asymmetric synthesis pf protected α-hydroxy-amino aldehydes and acids
Öppna denna publikation i ny flik eller fönster >>Practical amino acid-catalyzed asymmetric synthesis pf protected α-hydroxy-amino aldehydes and acids
(Engelska)Manuskript (preprint) (Övrigt vetenskapligt)
Nationell ämneskategori
Annan medicinsk grundvetenskap
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-39028 (URN)
Tillgänglig från: 2010-05-06 Skapad: 2010-05-06 Senast uppdaterad: 2018-01-12Bibliografiskt granskad

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