Total Synthesis of the Formamicin Aglycon, Formamicinone

The total synthesis of formamicinone (2), the aglycone of formamicin (1), has been accomplished via the late-stage Suzuki cross-coupling of fragments 5 and 6, the macrolactonization of seco ester 14, and the Mukaiyama aldol reaction of aldehyde 3 and methyl ketone 4. An efficient and highly stereose...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 3; pp. 377 - 379
Main Authors Savall, Brad M, Blanchard, Nicolas, Roush, William R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.02.2003
Amer Chemical Soc
Subjects
Anti-Bacterial Agents - chemistry
Chemistry
Chemistry, Organic
Macrolides
Molecular Structure
Physical Sciences
Science & Technology
KETONES
ALDOL REACTIONS
CROSS-COUPLING REACTIONS
SACCHAROTHRIX SP
STRAIN
ELAIOPHYLIN
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Summary:The total synthesis of formamicinone (2), the aglycone of formamicin (1), has been accomplished via the late-stage Suzuki cross-coupling of fragments 5 and 6, the macrolactonization of seco ester 14, and the Mukaiyama aldol reaction of aldehyde 3 and methyl ketone 4. An efficient and highly stereoselective second generation synthesis of vinyl iodide 6 is also described.
Bibliography:Medline
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027569k