Application of the Intramolecular Vinylogous Morita−Baylis−Hillman Reaction toward the Synthesis of the Spinosyn A Tricyclic Nucleus

A concise synthesis of the spinosyn A tricyclic nucleus 27 has been developed by a route featuring a one-pot tandem intramolecular Diels−Alder reaction and intramolecular vinylogous Morita−Baylis−Hillman cyclization in which five stereocenters in tricycle 10 are set with excellent selectivity.

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 18; pp. 3157 - 3160
Main Authors Mergott, Dustin J, Frank, Scott A, Roush, William R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.09.2002
Amer Chemical Soc
Subjects
Anti-Bacterial Agents - chemical synthesis
Chemistry
Chemistry, Organic
Cyclization
Insecticides - chemical synthesis
Macrolides
Physical Sciences
Saccharopolyspora - chemistry
Science & Technology
Stereoisomerism
Vinyl Compounds - chemistry
ALCOHOLS
CHEMISTRY
BOTTOM-HALF
ENANTIOSELECTIVE SYNTHESIS
STEREOCONTROL
CHLOROTHRICOLIDE
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Summary:A concise synthesis of the spinosyn A tricyclic nucleus 27 has been developed by a route featuring a one-pot tandem intramolecular Diels−Alder reaction and intramolecular vinylogous Morita−Baylis−Hillman cyclization in which five stereocenters in tricycle 10 are set with excellent selectivity.
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/ol026540d