Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 17
246
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

New, Efficient, and High-Yielding Asymmetric Synthesis of (4S,5S)-Cytoxazone

, , , &
Pages 2624-2631 | Received 28 Dec 2010, Published online: 29 May 2012
 

Abstract

A new approach for the asymmetric synthesis of (4S,5S)-cytoxazone 1 in five steps and in 48% overall yield starting from commercially available (R)-epichlorohydrin has been described. The key step include stereoselective 1,2-addition of p-methoxyphenyl magnesium bromide (p-OMePhMgBr) to chiral N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, which gave corresponding sulfinamide 2 with high diastereoselectivity. Deprotection of the t-butylsulfonyl group and 1,3-dimethyl acetal in a single step followed by N-Boc protection and subsequent carbonylation yields the targeted (4S,5S)-cytoxazone 1.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENT

Financial support from the Inogent Laboratories Private Limited (A GVK BIO Company) is gratefully acknowledged.

Notes

a Yields in parentheses are for recovered starting materials.

Log in via your institution

Log in to Taylor & Francis Online

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 422.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.