A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically Controlled Ring-Closing-Metathesis Reaction of a Densely Functionalized Diene

A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically Controlled Ring-Closing-Metathesis Reaction of a Densely Functionalized Diene

Der Schlüsselschritt in einer formalen Totalsynthese von Eleutherobin war die bisher unbekannte kinetisch kontrollierte RCM‐Reaktion des hochfunktionalisierten Diens 1 mit zwei PMP‐geschützten Allylalkoholeinheiten in Gegenwart eines Grubbs‐Katalysators der zweiten Generation. Isomerisierung des 10‐...

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Bibliographic Details
Published in:Angewandte Chemie Vol. 117; no. 4; pp. 594 - 597
Main Authors: Castoldi, Damiano, Caggiano, Lorenzo, Panigada, Laura, Sharon, Ofer, Costa, Anna M., Gennari, Cesare
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 14-01-2005
WILEY‐VCH Verlag
Subjects:
Asymmetrische Synthesen
Metathese
Naturstoffe
Totalsynthesen
Tumortherapeutika
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Summary:Der Schlüsselschritt in einer formalen Totalsynthese von Eleutherobin war die bisher unbekannte kinetisch kontrollierte RCM‐Reaktion des hochfunktionalisierten Diens 1 mit zwei PMP‐geschützten Allylalkoholeinheiten in Gegenwart eines Grubbs‐Katalysators der zweiten Generation. Isomerisierung des 10‐gliedrigen E‐Endions 2 zum stabileren Z‐Isomer und Abspaltung der Alkoholschutzgruppe führte zur bekannten Vorstufe 3. PMP=p‐Methoxyphenyl.
Bibliography:We thank the European Commission for financial support (IHP Network grant "Design and synthesis of microtubule stabilizing anticancer agents" HPRN-CT-2000-00018) and for postdoctoral fellowships to L. C. (HPRN-CT-2000-00018) and O. S. ("Marie Curie" MEIF-CT-2003-500880). We also thank "Merck Research Laboratories" (Merck's Academic Development Program Award to C. G.) and Università degli Studi di Milano for financial support and for a graduate fellowship (to D. Castoldi). We thank Dr. Raphael Beumer, Dr. Pau Bayón, Dr. Joachim Telser, and Dr. Fabienne Pradaux for preliminary experiments related to this work, as well as Dr. Nicola Mongelli (Nerviano Medical Science) and Prof. Jaume Vilarrasa (University of Barcelona) for inspiring discussions.
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ArticleID:ANGE200461767
istex:3A5969191DC364B3D0B79733B05A41B04827D22D
We thank the European Commission for financial support (IHP Network grant “Design and synthesis of microtubule stabilizing anticancer agents” HPRN‐CT‐2000‐00018) and for postdoctoral fellowships to L. C. (HPRN‐CT‐2000‐00018) and O. S. (“Marie Curie” MEIF‐CT‐2003‐500880). We also thank “Merck Research Laboratories” (Merck's Academic Development Program Award to C. G.) and Università degli Studi di Milano for financial support and for a graduate fellowship (to D. Castoldi). We thank Dr. Raphael Beumer, Dr. Pau Bayón, Dr. Joachim Telser, and Dr. Fabienne Pradaux for preliminary experiments related to this work, as well as Dr. Nicola Mongelli (Nerviano Medical Science) and Prof. Jaume Vilarrasa (University of Barcelona) for inspiring discussions.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.200461767