Palladium(0)-Mediated Desymmetrization of Meso Tetraols:  An Approach to the C3−C17 Bis-oxane Segment of Phorboxazoles A and B

meso-Tetraol bis(allylic acetates) 2 and 5 were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled desymmetrization provided the desired bis-oxanes in greater than 98% ee. Bis-oxanes 1 and 4 represent potential synthetic intermediates for the C3−C17 subunits of...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 5; no. 21; pp. 3915 - 3918
Main Authors Lucas, Brian S, Burke, Steven D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.10.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclization
Heterocyclic Compounds, 4 or More Rings - chemistry
Models, Chemical
Molecular Structure
Oxazoles - chemistry
Palladium - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
HALICHONDRIN-B
SPONGE PHORBAS SP
NATURAL-PRODUCT SYNTHESIS
ASYMMETRIC-SYNTHESIS
ABSOLUTE-CONFIGURATION
STEREOSELECTIVE-SYNTHESIS
PETASIS-FERRIER REARRANGEMENT
CONVERGENT SYNTHESIS
2-DIRECTIONAL CHAIN SYNTHESIS
MARINE SPONGE
Online AccessGet full text

Cover

More Information
Summary:meso-Tetraol bis(allylic acetates) 2 and 5 were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled desymmetrization provided the desired bis-oxanes in greater than 98% ee. Bis-oxanes 1 and 4 represent potential synthetic intermediates for the C3−C17 subunits of phorboxazoles A and B.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0354775