Issue 39, 2013
From the journal:

Organic & Biomolecular Chemistry

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

Gullapalli Kumaraswamy,*a   Akula Narayana Murthy,ab   Vykunthapu Narayanarao,a   Sahithya Phani Babu Vemulapallic  and  Jagadeesh Bharatamc  

* Corresponding authors

a Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 607, India
E-mail: gkswamy_iict@yahoo.co.in
Fax: +91-40-27193275
Tel: +91-40-27193154

b An Associate Institution of University of Hyderabad, Hyderabad-500 046, India

c Center for NMR & Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 607, India

Abstract

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.

Graphical abstract: 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

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Article information

DOI
https://doi.org/10.1039/C3OB41088A
Article type
Paper
Submitted
30 May 2013
Accepted
08 Aug 2013
First published
08 Aug 2013

Org. Biomol. Chem., 2013,11, 6751-6765

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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

G. Kumaraswamy, A. Narayana Murthy, V. Narayanarao, S. P. B. Vemulapalli and J. Bharatam, Org. Biomol. Chem., 2013, 11, 6751 DOI: 10.1039/C3OB41088A

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