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Amino Aacohols: stereoselective synthesis and applications in diversity-oriented synthesis
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
2005 (English)Licentiate thesis, comprehensive summary (Other scientific)
Abstract [en]

This thesis is divided into three separate parts with amino alcohols as the common feature. The first part describes the development of a novel three-component approach to the synthesis of α-hydroxy-β-amino esters. Utilizing a highly diastereoselective Rh(II)-catalyzed 1,3-dipolar cycloaddition of carbonyl ylides to various aldimines, syn-α-hydroxy-β-amino esters formed in high yields and excellent diastereoselectivities. This methodology was also applied in a short enantioselective synthesis of the C-13 side-chain of Taxol.

The second part of the thesis describes a total synthesis of D-erythro- Sphingosine based on a cross-metathesis approach to assemble the polar head group and the aliphatic chain.

The last part deals with the application of amino alcohols as scaffolds in a diversity-oriented protocol for the development of libraries of small polycyclic molecules. The design of the libraries is based on the iterative use of two powerful ring-forming reactions; a ring-closing metathesis and an intramolecular Diels-Alder reaction, to simultaneously introduce structural complexity and diversity.

Place, publisher, year, edition, pages
Stockholm: KTH , 2005. , 41 p.
Series
Trita-IOK, ISSN 1100-7974 ; 05.95
Keyword [en]
Organic chemistry, amino alcohol, carbenoid, carbonyl ylide, cross-metathesis, diastereoselective, 1, 3-dipolar cycloaddition, sphingosine
Keyword [sv]
Organisk kemi
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-315ISBN: 91-7178-006-8 (print)OAI: oai:DiVA.org:kth-315DiVA: diva2:8915
Presentation
2005-05-09, Sal D41, Lindstedtsvägen 17, Stockholm, 10:00
Supervisors
Note
QC 20101222Available from: 2005-07-18 Created: 2005-07-18 Last updated: 2010-12-22Bibliographically approved
List of papers
1. 1,3-Dipolar Cycloadditions of Carbonyl Ylides to Aldimines: A Three Component Approach to syn-α-Hydroxy-β-amino Esters
Open this publication in new window or tab >>1,3-Dipolar Cycloadditions of Carbonyl Ylides to Aldimines: A Three Component Approach to syn-α-Hydroxy-β-amino Esters
2005 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 44, no 20, 3096-3099 p.Article in journal (Refereed) Published
Abstract [en]

(Chemical Equation Presented) A highly diastereoselective Rh II-catalyzed 1,3-dipolar cycloaddition leads to the formation of syn-β-amino alcohols and syn-α-hydroxy-β-amino acids in high yields (see scheme; p-TSA = poro-toluenesulfonic acid, Bn = benzyl). This three-component approach to the addition of metal-associated carbonyl ylides to aldimines was applied to a short enantioselective synthesis of the C13 side chain of taxol.

Keyword
amino alcohols; carbenoids; cycloaddition; multicomponent reactions; ylides
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-7403 (URN)10.1002/anie.200500296 (DOI)000229342600020 ()2-s2.0-18944380156 (Scopus ID)
Note
QC 20100817Available from: 2007-08-23 Created: 2007-08-23 Last updated: 2010-12-22Bibliographically approved
2. A Practical Synthesis of D-erythro-Sphingosine Using a Cross-Metathesis Approach
Open this publication in new window or tab >>A Practical Synthesis of D-erythro-Sphingosine Using a Cross-Metathesis Approach
2004 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 2, no 11, 1643-1646 p.Article in journal (Refereed) Published
Abstract [en]

Starting from a vinylepoxide, a short and practical synthesis of D-erythro-sphingosine is described. The key transformations are a regioselective opening of the vinylepoxide and an E-selective cross-metathesis, affording the target molecule in 5 steps and 51% overall yield.

Keyword
ring-closing metathesis, glycosphingolipid precursors, stereoselective synthesis, ceramide, epoxy-4-pentenols, diastereomers, selectivity, alcohols, products, support
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-7406 (URN)10.1039/b403568b (DOI)000221664600014 ()2-s2.0-2942752245 (Scopus ID)
Note
QC 20100825Available from: 2007-08-23 Created: 2007-08-23 Last updated: 2010-12-22Bibliographically approved

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