Total synthesis of dehydroambliol-A and its unnatural Z isomer

Convergent total syntheses of dehydroambliol-A (1a), its unnatural Z isomer 1b, and ambliofuran (2) are described. The syntheses utilized 2-(3'-furyl)-1,3-dithiane (6) as a common intermediate. Analysis of their proton and carbon magnetic resonance spectra confirm that in the natural product de...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 56; no. 9; pp. 3102 - 3108
Main Authors Magatti, Charles V., Kaminski, James J., Rothberg, Irvin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.04.1991
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Dithioacetal
Trienic compound
Dienic compound
Oxygen heterocycle
Total synthesis
Thioaldehyde
Cis stereoisomer
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Summary:Convergent total syntheses of dehydroambliol-A (1a), its unnatural Z isomer 1b, and ambliofuran (2) are described. The syntheses utilized 2-(3'-furyl)-1,3-dithiane (6) as a common intermediate. Analysis of their proton and carbon magnetic resonance spectra confirm that in the natural product dehydroambliol-A and in synthetic dehydroambliol-A the DELTA-7-bond possesses the E geometry, while in the unnatural isomer of dehydroambliol-A, the DELTA-7-bond is of the Z configuration.
Bibliography:ark:/67375/TPS-DHK4J364-X
istex:E2D8FBEAA68A10792E78CAFC6476FABEA2184968
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00009a033