Amino Aacohols : stereoselective synthesis and applications in diversity-oriented synthesis

• Main Author: Torssell, Staffan
• Format: Others
• Language: English
• Published: KTH, Kemi 2005
• Subjects: Organic chemistry; amino alcohol; carbenoid; carbonyl ylide; cross-metathesis; diastereoselective; 1; 3-dipolar cycloaddition; sphingosine; Organisk kemi
• Online Access: http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-315; http://nbn-resolving.de/urn:isbn:91-7178-006-8

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. === QC 20101222