Redox Refunctionalization of Steroid Spiroketals. Structure Correction of Ritterazine M

The structure of the North spiroketal moiety of ritterazine M has been corrected from 1a to 1b. This was accomplished by comparison of published spectra of the natural product with five synthetic spiroketal−alcohols. Synthesis of these models was efficiently accomplished by reductive cleavage of the...

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 3; pp. 313 - 316
Main Authors Lee, Seongmin, LaCour, Thomas G, Lantrip, Douglas, Fuchs, Philip L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.02.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Molecular Structure
Oxidation-Reduction
Phenazines
Physical Sciences
Science & Technology
Spiro Compounds - chemistry
Steroids - chemistry
INTRAMOLECULAR HYDROGEN ABSTRACTION
ACYCLIC COMPOUNDS
UNIT
CREATION
CEPHALOSTATIN SYNTHESIS
SPIROACETALS
UNIVERSAL NMR DATABASE
RADICAL GENERATION
ACETATE
STEREOCHEMICAL ASSIGNMENT
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Summary:The structure of the North spiroketal moiety of ritterazine M has been corrected from 1a to 1b. This was accomplished by comparison of published spectra of the natural product with five synthetic spiroketal−alcohols. Synthesis of these models was efficiently accomplished by reductive cleavage of the spiroketal and Sharpless asymmetric dihydroxylation of an isopentyl, methyl 1,1-disubstituted olefin, followed by Suarez iodine[III] oxidative spirocyclization of monoprotected 1°,3° 1,2 diols.
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/ol0165894