A Short and Efficient Synthesis of Neodysiherbaine A by Using Catalytic Oxidative Cyclization

To the point: The synthesis of the title compound was achieved with 24 % overall yield through a sequence that has just seven linear steps (see scheme). Key points are the facial selectivity displayed by an oxocarbenium ion derived from a ribopyranose system and an osmium‐catalyzed oxidative cycliza...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 50; no. 33; pp. 7604 - 7606
Main Authors Donohoe, Timothy J., Winship, Paul C. M., Tatton, Matthew R., Szeto, Peter
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 08.08.2011
WILEY‐VCH Verlag
Wiley
Subjects
Alanine - analogs & derivatives
Alanine - chemical synthesis
Alanine - chemistry
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
Cyclization
Models, Molecular
Molecular Conformation
natural products
osmium
Oxidation-Reduction
oxidative cyclization
oxocarbenium ions
Physical Sciences
Science & Technology
Stereoisomerism
total synthesis
oxocarbenium ions
DYSIHERBAINE
ANALOGS
osmium
C-GLYCOSIDES
oxidative cyclization
MARINE SPONGE
KAINATE RECEPTORS
natural products
DIOLS
AMINO-ACIDS
PHARMACOLOGICAL-ACTIVITY
total synthesis
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Summary:To the point: The synthesis of the title compound was achieved with 24 % overall yield through a sequence that has just seven linear steps (see scheme). Key points are the facial selectivity displayed by an oxocarbenium ion derived from a ribopyranose system and an osmium‐catalyzed oxidative cyclization that is compatible with several acid‐sensitive groups.
Bibliography:EPSRC
GlaxoSmithKline
We would like to thank the EPSRC/Pharma Organic Synthetic Chemistry Studentships program for supporting this project and GlaxoSmithKline for financial support. We also thank Diamond Light Source for an award of beamtime on I19 (MT1858) and Dr. K. E. Christensen for support.
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ark:/67375/WNG-DFXN189F-B
ArticleID:ANIE201102525
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201102525