Stereocontrolled Total Synthesis of (−)-Kaitocephalin

This paper describes the successful implementation of a stereocontrolled strategy for the total chemical synthesis of the pyrrolidine-based alkaloid (−)-kaitocephalin. This scalable synthetic route profits from the strategic utilization of substrate-controlled manipulations for the iterative install...

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Veröffentlicht in:	Journal of organic chemistry 2008-03, Vol.73 (5), p.1661-1681
Hauptverfasser:	Vaswani, Rishi G, Chamberlin, A. Richard
Format:	Artikel
Sprache:	eng
Schlagworte:	Acylation Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Magnetic Resonance Spectroscopy Mass Spectrometry Models, Chemical Organic chemistry Oxidation-Reduction Preparations and properties Pyrroles - chemical synthesis Pyrroles - chemistry Stereoisomerism
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creator	Vaswani, Rishi G Chamberlin, A. Richard
description	This paper describes the successful implementation of a stereocontrolled strategy for the total chemical synthesis of the pyrrolidine-based alkaloid (−)-kaitocephalin. This scalable synthetic route profits from the strategic utilization of substrate-controlled manipulations for the iterative installation of the requisite stereogenic centers. The key transformations include a diastereoselective modified Claisen condensation, a chemo- and diastereoselective reduction of a β-keto ester, and the substrate-directed hydrogenation of a dehydroamino ester derivative. During the course of our investigations, an interesting stereoconvergent cyclization reaction was discovered for the efficient assembly of the kaitocephalin 2,2,5-trisubstituted pyrrolidine core.
doi_str_mv	10.1021/jo702329z
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Richard</creatorcontrib><title>Stereocontrolled Total Synthesis of (−)-Kaitocephalin</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>This paper describes the successful implementation of a stereocontrolled strategy for the total chemical synthesis of the pyrrolidine-based alkaloid (−)-kaitocephalin. This scalable synthetic route profits from the strategic utilization of substrate-controlled manipulations for the iterative installation of the requisite stereogenic centers. The key transformations include a diastereoselective modified Claisen condensation, a chemo- and diastereoselective reduction of a β-keto ester, and the substrate-directed hydrogenation of a dehydroamino ester derivative. 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Richard</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vaswani, Rishi G</au><au>Chamberlin, A. Richard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereocontrolled Total Synthesis of (−)-Kaitocephalin</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-03-07</date><risdate>2008</risdate><volume>73</volume><issue>5</issue><spage>1661</spage><epage>1681</epage><pages>1661-1681</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>This paper describes the successful implementation of a stereocontrolled strategy for the total chemical synthesis of the pyrrolidine-based alkaloid (−)-kaitocephalin. This scalable synthetic route profits from the strategic utilization of substrate-controlled manipulations for the iterative installation of the requisite stereogenic centers. The key transformations include a diastereoselective modified Claisen condensation, a chemo- and diastereoselective reduction of a β-keto ester, and the substrate-directed hydrogenation of a dehydroamino ester derivative. 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subjects	Acylation Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Magnetic Resonance Spectroscopy Mass Spectrometry Models, Chemical Organic chemistry Oxidation-Reduction Preparations and properties Pyrroles - chemical synthesis Pyrroles - chemistry Stereoisomerism
title	Stereocontrolled Total Synthesis of (−)-Kaitocephalin
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