Organocatalytic enantioselective synthesis of 1,3,5-polyols by means of iterative asymmetric epoxidation: their application to the total synthesis of polyrhacitide A

We have developed a pragmatic route to the stereogenic skipped 1,3,5-polyols. The strategic transformation includes an organocatalytic enantioselective asymmetric epoxidation, which is either syn- or anti-selective as genesis of chirality and successive SN2 opening reaction by an appropriate functio...

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Bibliographic Details
Published in:Tetrahedron 2012-04, Vol.68 (15), p.3179-3186
Main Authors: Kumaraswamy, Gullapalli, Murthy, Akula Narayana, Sadaiah, Kadivendi
Format: Article
Language:English
Subjects:
Asymmetry
Catalysis
Catalysts: preparations and properties
Chemistry
Chirality
Epoxidation
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Hydroboration
Kinetics and mechanisms
Nucleophiles
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Synthesis (chemistry)
Tetrahedrons
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Transformations
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Summary:We have developed a pragmatic route to the stereogenic skipped 1,3,5-polyols. The strategic transformation includes an organocatalytic enantioselective asymmetric epoxidation, which is either syn- or anti-selective as genesis of chirality and successive SN2 opening reaction by an appropriate functionalized nucleophile, followed by hydroboration/oxidation to generate stereoisomers in good yield. The critical intermediate generated en route to this process is employed in the total synthesis of polyrhacitide A. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.02.055