Enantioselective synthesis of δ-/γ-alkoxy-β-hydroxy-α-alkyl-substituted Weinreb amides via DKR-ATH: application to the synthesis of advanced intermediate of (-)-brevisamide

A method of preparing stereodefined δ-/γ-alkoxy-β-hydroxy-α-alkyl-substituted Weinreb amides containing two successive hydroxyl-alkyl stereocenters has been developed. Further, this strategy coupled with organo-catalyzed asymmetric epoxidation culminates in the synthesis of a critical intermediate o...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2013-10, Vol.11 (39), p.6751-6765
Main Authors: Kumaraswamy, Gullapalli, Narayana Murthy, Akula, Narayanarao, Vykunthapu, Vemulapalli, Sahithya Phani Babu, Bharatam, Jagadeesh
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Alkaloids - chemical synthesis
Alkaloids - chemistry
Alkylation
Amides - chemical synthesis
Catalysis
Epoxy Compounds - chemistry
Hydroxylation
Molecular Structure
Pyrans - chemical synthesis
Pyrans - chemistry
Stereoisomerism
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Summary:A method of preparing stereodefined δ-/γ-alkoxy-β-hydroxy-α-alkyl-substituted Weinreb amides containing two successive hydroxyl-alkyl stereocenters has been developed. Further, this strategy coupled with organo-catalyzed asymmetric epoxidation culminates in the synthesis of a critical intermediate of (-)-brevisamide and its diastereomers.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob41088a