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.

PDF Jou_Org_Che_81-22_11363_2016.pdf - Published Version Restricted to Registered users only Download (912kB) | Request a copy

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
Publication:	JOURNAL OF ORGANIC CHEMISTRY
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
Date Deposited:	10 Feb 2017 10:03
Last Modified:	10 Feb 2017 10:03
URI:	http://eprints.iisc.ac.in/id/eprint/56221

Actions (login required)

View Item