Stereo- and Regioselective Synthesis of 2-Amino-3,5-diols via Stereospecific Crotyl Transfer and Regioselective Aminohydroxylation

Abstract A short synthesis of 2-amino-3,5-diols is described, including the all- S isomer enigmol, a synthetic anticancer compound inspired by the structure of fumonisin B 1 . The synthetic route features 1) stereospecific crotyl transfer to tetradecanal via pericyclic oxonia-Cope rearrangement; 2)...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2012-12, Vol.44 (23), p.3639-3648
Main Authors: McDonald, Frank E., Pereira, Claney L.
Format: Article
Language:English
Subjects:
Antineoplastic agents
Biological and medical sciences
Chemistry
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
General aspects
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lipids
Medical sciences
Microbiology
Mycology
Organic chemistry
Pathogenicity, host-agent relations, miscellaneous strains, epidemiology
Pharmacology. Drug treatments
Preparations and properties
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Summary:Abstract A short synthesis of 2-amino-3,5-diols is described, including the all- S isomer enigmol, a synthetic anticancer compound inspired by the structure of fumonisin B 1 . The synthetic route features 1) stereospecific crotyl transfer to tetradecanal via pericyclic oxonia-Cope rearrangement; 2) stereoselective epoxidation of the alkene; 3) regioselective epoxide opening with azide; and 4) reduction of azide to amine. This manuscript also corrects a structure assignment error in a previously reported synthesis of one of the diastereomers of enigmol.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0032-1316805