A Biomimetically Inspired Synthesis of the Dehydropiperidine Domain of Thiostrepton

The key step in the dimerization of the azadiene 1 is a hetero‐Diels–Alder reaction. The product 2 constitutes the dehydropiperidine core of the antibiotic thiostrepton.

Saved in:
Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 41; no. 11; pp. 1941 - 1945
Main Authors Nicolaou, K. C., Nevalainen, Marta, Safina, Brian S., Zak, Mark, Bulat, Stephan
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 03.06.2002
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
antibiotics
asymmetric synthesis
Biomimetics
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
cycloaddition
Molecular Conformation
natural products
Physical Sciences
Piperidines - chemistry
Science & Technology
Thiostrepton - chemical synthesis
Thiostrepton - chemistry
total synthesis
natural products
asymmetric synthesis
cycloaddition
DIELS-ALDER REACTIONS
ACIDS
total synthesis
N-(ARYLMETHYLENE)DEHYDROALANINE METHYL-ESTERS
antibiotics
Online AccessGet full text

Cover

More Information
Summary:The key step in the dimerization of the azadiene 1 is a hetero‐Diels–Alder reaction. The product 2 constitutes the dehydropiperidine core of the antibiotic thiostrepton.
Bibliography:istex:B2AC885295E364344AB9B62AB6A583EACBFF33AF
ark:/67375/WNG-84S8J7RV-T
ArticleID:ANIE1941
We thank Drs. D. H. Huang and L. Pasternack, G. Suizdak, and R. Chadja for NMR spectroscopic, mass spectrometric, and X‐ray crystallographic assistance, respectively. Financial support for this work was provided by The Skaggs Institute for Chemical Biology, the National Institutes of Health (USA), fellowships from The Academy of Finland (M.N.), The Skaggs Institute for Research (M.Z.), and Bayer AG (S.B.), and grants from Abbott, Amgen, Array Biopharma, Boehringer‐Ingelheim, Glaxo, Hoffmann‐LaRoche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020603)41:11<1941::AID-ANIE1941>3.0.CO;2-V