Journal article
Stereoselective Mn-mediated coupling of functionalized iodides and hydrazones: a synthetic entry to the tubulysin gamma-amino acids
Organic letters, Vol.6(19), pp.3249-3252
09/16/2004
DOI: 10.1021/ol048986v
PMID: 15355024
Abstract
[structure: see text] Synthesis of gamma-amino acids, important building blocks in bioorganic and natural product chemistry, is accomplished using a stereoselective carbon-carbon bond construction of the chiral amine. Alkyl iodides and chiral hydrazones with protected alcohol functionality are coupled via highly diastereoselective photolytic Mn-mediated addition to the C=N bond, providing access to enantiomerically pure multifunctional chiral alpha-branched amines. Reductive N-N bond cleavage and alcohol oxidation provides alpha-substituted gamma-amino acid building blocks for tubulysin D.
Details
- Title: Subtitle
- Stereoselective Mn-mediated coupling of functionalized iodides and hydrazones: a synthetic entry to the tubulysin gamma-amino acids
- Creators
- Gregory K Friestad - Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA. gregory.friestad@uvm.eduJean-Charles MariéAmy M Deveau
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.6(19), pp.3249-3252
- Publisher
- United States
- DOI
- 10.1021/ol048986v
- PMID
- 15355024
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Grant note
- GM-67187 / NIGMS NIH HHS
- Language
- English
- Date published
- 09/16/2004
- Academic Unit
- Chemistry
- Record Identifier
- 9983985713102771
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