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Synthesis of beta-Amino-Substituted Enones by Addition of Substituted Methyl Enones to Sulfinimines: Application to the Total Synthesis of Alkaloids (+)-Lasubine II and (+)-241D and the Formal Total Synthesis of (-)-Lasubine I

Reddy, Arava Amaranadha and Reddy, Polimera Obula and Prasad, Kavirayani R (2016) Synthesis of beta-Amino-Substituted Enones by Addition of Substituted Methyl Enones to Sulfinimines: Application to the Total Synthesis of Alkaloids (+)-Lasubine II and (+)-241D and the Formal Total Synthesis of (-)-Lasubine I. In: JOURNAL OF ORGANIC CHEMISTRY, 81 (22). pp. 11363-11371.

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Official URL: http://dx.doi.org/10.1021/acsjoc.6b01541

Abstract

Addition of silyl enol ethers obtained from substituted methyl enones to chiral sulfinimines afforded the beta-amino-substituted enones with excellent selectivity. Utility of the obtained N-sulfinyl beta-amino ketones possessing a,alpha,beta-unsaturation is exemplified in the total synthesis of the quinolizidine alkaloid natural products (-)-lasubine I, (+)-lasubine II, and substituted piperidine alkaloid (+)-241-D.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 10 Feb 2017 10:03
Last Modified: 10 Feb 2017 10:03
URI: http://eprints.iisc.ac.in/id/eprint/56221

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