The Antibody Catalysis Route to the Total Synthesis of Epothilones

An efficient monoclonal aldolase antibody that proceeds by an enamine mechanism was generated by reactive immunization. Here, this catalyst has been used in the total synthesis of epothilones A (1) and C (3). The starting materials for the synthesis of these molecules have been obtained by using ant...

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Veröffentlicht in:	Proceedings of the National Academy of Sciences - PNAS 1998-12, Vol.95 (25), p.14603-14608
Hauptverfasser:	Sinha, Subhash C., Barbas, Carlos F., Lerner, Richard A.
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols Aldehydes Antibodies Antibodies, Catalytic - chemistry Antibodies, Catalytic - immunology Catalysts Enantiomers Epothilones Epoxy Compounds - chemical synthesis Epoxy Compounds - chemistry Fructose-Bisphosphate Aldolase - chemistry Fructose-Bisphosphate Aldolase - immunology Isomers Molecular biology Molecules Organic chemistry Physical Sciences Room temperature Tetrahedrons Thiazoles - chemical synthesis Thiazoles - chemistry
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Beschreibung
Zusammenfassung:	An efficient monoclonal aldolase antibody that proceeds by an enamine mechanism was generated by reactive immunization. Here, this catalyst has been used in the total synthesis of epothilones A (1) and C (3). The starting materials for the synthesis of these molecules have been obtained by using antibody-catalyzed aldol and retro-aldol reactions. These precursors were then converted to epothilones A (1) and C (3) to complete the total synthesis.
ISSN:	0027-8424 1091-6490
DOI:	10.1073/pnas.95.25.14603