Asymmetric syntheses of the stereotetrads of Amphotericin B and Calyculin C

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en
dc.contributor.author Karisalmi, Kaisa
dc.date.accessioned 2012-02-13T13:01:53Z
dc.date.available 2012-02-13T13:01:53Z
dc.date.issued 2004-11-13
dc.identifier.isbn 951-22-7300-4
dc.identifier.issn 1236-2999
dc.identifier.uri https://aaltodoc.aalto.fi/handle/123456789/2471
dc.description.abstract Calyculin C and Amphotericin B are biologically active natural products. Amphotericin B is an antifungal agent, which has been a widely used drug in antifungal chemotherapy. Calyculin C is a potent protein phosphatase inhibitor and plays an important role in cancer research. Calyculin C and Amphotericin B contain a stereotetrad fragment. The synthesis of the syn, anti, anti stereotetrad of Amphotericin B was based on the thiopyranone ring and a chiral auxiliary strategies. The synthesis began with the introduction of the asymmetry into the thiopyranone ring via a tartrate derived chiral ortho ester, followed by a highly diastereoselective Mukaiyama aldol reaction and 1,3-syn diol reduction. The synthesis was complete in only six steps with reasonable yield and diastereoselectivity. The all-anti stereotetrad of Calyculin C was first approached through a convergent strategy but it yielded a wrong diastereomer as the major product. The linear synthesis began with a chiral boron crotylation followed by ozonolysis. The second crotylation with (Z)-crotyl trifluorosilane produced the desired anti, anti, anti stereochemistry with high diastereoselectivity. en
dc.format.extent 55, [26]
dc.format.mimetype application/pdf
dc.language.iso en en
dc.publisher Helsinki University of Technology en
dc.publisher Teknillinen korkeakoulu fi
dc.relation.ispartofseries Organic chemistry report en
dc.relation.ispartofseries 3/2004 en
dc.relation.haspart Karisalmi K., Koskinen A. M. P., Nissinen M. and Rissanen K., 2003. Model studies on a diastereoselective synthesis of the C(33)-C(37) fragment of Amphotericin B. Tetrahedron 59, number 9, pages 1421-1427. [article1.pdf] © 2003 Elsevier Science. By permission.
dc.relation.haspart Karisalmi K., Rissanen K. and Koskinen A. M. P., 2003. An enantioselective synthesis of the C(33)-C(37) fragment of Amphotericin B. Organic & Biomolecular Chemistry 1, number 18, pages 3193-3196.
dc.relation.haspart Karisalmi K. and Koskinen A. M. P., 2004. Studies towards the synthesis of the C(9)-C(20) lactone-dipropionate fragment of Calyculin C. Synthesis 2004, number 9, pages 1331-1341.
dc.relation.haspart Karisalmi K. and Koskinen A. M. P., 2004. Stereoselective synthesis of the C<sub>9</sub>-C<sub>19</sub> lactone-dipropionate fragment of calyculin C. Tetrahedron Letters 45, in press. [article4.pdf] © 2004 Elsevier Science. By permission.
dc.subject.other Chemistry en
dc.title Asymmetric syntheses of the stereotetrads of Amphotericin B and Calyculin C en
dc.type G5 Artikkeliväitöskirja fi
dc.description.version reviewed en
dc.contributor.department Department of Chemical Technology en
dc.contributor.department Kemian tekniikan osasto fi
dc.subject.keyword polyketides en
dc.subject.keyword polypropionates en
dc.subject.keyword asymmetric synthesis en
dc.subject.keyword stereotetrad en
dc.subject.keyword Calyculin C en
dc.subject.keyword Amphotericin B en
dc.identifier.urn urn:nbn:fi:tkk-004345
dc.type.dcmitype text en
dc.type.ontasot Väitöskirja (artikkeli) fi
dc.type.ontasot Doctoral dissertation (article-based) en
dc.contributor.lab Laboratory of Organic Chemistry en
dc.contributor.lab Orgaanisen kemian laboratorio fi


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