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; Yoshinori Fujimoto

doi:10.1007/s11696-020-01462-1

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, Yoshinori Fujimoto

Department of Agricultural Chemistry

Research output: Contribution to journal › Article › peer-review

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: [Figure not available: see fulltext.]

Original language	English
Journal	Chemical Papers
DOIs	https://doi.org/10.1007/s11696-020-01462-1
Publication status	Accepted/In press - 2021

Keywords

Absolute stereochemistry
Mosher’s method
Naphthoquinone
Solaniol

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title = "Determination of the absolute stereochemistry of (+)-solaniol",

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{\textquoteright}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: [Figure not available: see fulltext.]",

keywords = "Absolute stereochemistry, Mosher{\textquoteright}s method, Naphthoquinone, Solaniol",

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

year = "2021",

doi = "10.1007/s11696-020-01462-1",

language = "English",

journal = "Chemical Papers",

issn = "0366-6352",

publisher = "Springer International Publishing AG",

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TY - JOUR

T1 - Determination of the absolute stereochemistry of (+)-solaniol

AU - Kehelpannala, Cheka

AU - Rathnayake, G. R.Nalin

AU - Dissanayake, Dilhara

AU - Kanatiwela, Dinusha

AU - Kumar, N. Savitri

AU - Adikaram, Nimal

AU - Jayasinghe, Lalith

AU - Araya, Hiroshi

AU - Fujimoto, Yoshinori

PY - 2021

Y1 - 2021

N2 - 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: [Figure not available: see fulltext.]

AB - 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: [Figure not available: see fulltext.]

KW - Absolute stereochemistry

KW - Mosher’s method

KW - Naphthoquinone

KW - Solaniol

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U2 - 10.1007/s11696-020-01462-1

DO - 10.1007/s11696-020-01462-1

M3 - Article

AN - SCOPUS:85098657265

JO - Chemical Papers

JF - Chemical Papers

SN - 0366-6352

ER -

Determination of the absolute stereochemistry of (+)-solaniol

Abstract

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