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Determination of the absolute stereochemistry of ( +)-solaniol

Cheka Kehelpannala, G. R. Nalin Rathnayake, Dilhara Dissanayake, Dinusha Kanatiwela, N. Savitri Kumar, Nimal Adikaram, Lalith Jayasinghe, Hiroshi Araya, and Yoshinori Fujimoto

National Institute of Fundamental Studies, Kandy, Sri Lanka

 

E-mail: lalith.ja@nifs.ac.lk

Received: 10 July 2020  Accepted: 1 December 2020

Abstract:

Abstract

The absolute stereochemistry of ( +)-solaniol (5,8-dihydroxy-7-(2-hydroxypropyl)-2-methoxy-6-methyl-1,4-naphthoquinone) (1) was deduced to be S using Mosher’s method. Our result did not accord with the R configuration of ( +)-solaniol recently proposed by Maharjan et al., but agreed with the S configuration determined by X-ray crystallographic analysis by Kyekyeku et al. In addition, complete and unambiguous assignments of 13C NMR signals for 1 are reported.

Graphic abstract

Keywords: Solaniol; Absolute stereochemistry; Mosher’s method; Naphthoquinone

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01462-1

 

Chemical Papers 75 (5) 2233–2235 (2021)

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