Total Synthesis of (−)-Okilactomycin

A highly convergent synthesis of (−)-okilactomycin is described. Key reactions of this synthesis include a strategy-level diastereoselective oxy-Cope rearrangement/oxidation sequence, a Petasis−Ferrier union/rearrangement tactic, and an efficient RCM reaction to construct the 13-membered macrocyclic...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 129; no. 48; pp. 14872 - 14874
Main Authors Smith, Amos B, Basu, Kallol, Bosanac, Todd
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.12.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
Lactones - chemical synthesis
Lactones - chemistry
Models, Molecular
Molecular Structure
Physical Sciences
Science & Technology
OXIDATION
DIELS-ALDER
CONSTRUCTION
CARBONYL-COMPOUNDS
ORGANIC HALIDES
ALDEHYDES
REARRANGEMENTS
DERIVATIVES
METATHESIS
OKILACTOMYCIN
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Summary:A highly convergent synthesis of (−)-okilactomycin is described. Key reactions of this synthesis include a strategy-level diastereoselective oxy-Cope rearrangement/oxidation sequence, a Petasis−Ferrier union/rearrangement tactic, and an efficient RCM reaction to construct the 13-membered macrocyclic ring.
Bibliography:ark:/67375/TPS-KPSC6WD3-4
istex:C93A447F8584962F320ACCF5EB45BD99B71B8DD6
Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja077569l