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
Pages (from-to)	2233-2235
Number of pages	3
Journal	Chemical Papers
Volume	75
Issue number	5
DOIs	https://doi.org/10.1007/s11696-020-01462-1
Publication status	Published - May 2021

Keywords

Absolute stereochemistry
Mosher’s method
Naphthoquinone
Solaniol

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10.1007/s11696-020-01462-1

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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",

note = "Publisher Copyright: {\textcopyright} 2021, Institute of Chemistry, Slovak Academy of Sciences.",

year = "2021",

month = may,

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

language = "English",

volume = "75",

pages = "2233--2235",

journal = "Chemical Papers",

issn = "0366-6352",

publisher = "Springer International Publishing AG",

number = "5",

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Determination of the absolute stereochemistry of (+)-solaniol. / Kehelpannala, Cheka; Rathnayake, G. R.Nalin; Dissanayake, Dilhara; Kanatiwela, Dinusha; Kumar, N. Savitri; Adikaram, Nimal; Jayasinghe, Lalith; Araya, Hiroshi; Fujimoto, Yoshinori.

In: Chemical Papers, Vol. 75, No. 5, 05.2021, p. 2233-2235.

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

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 - 2021/5

Y1 - 2021/5

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

VL - 75

SP - 2233

EP - 2235

JO - Chemical Papers

JF - Chemical Papers

SN - 0366-6352

IS - 5

ER -

Determination of the absolute stereochemistry of (+)-solaniol

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