A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

Research output: Contribution to journalJournal articlepeer-review

Standard

A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate. / Pedersen, Daniel Sejer; Robinson, Tony V; Taylor, Dennis K; Tiekink, Edward R T.

In: Journal of Organic Chemistry, Vol. 74, No. 11, 2009, p. 4400-4403.

Research output: Contribution to journalJournal articlepeer-review

Harvard

Pedersen, DS, Robinson, TV, Taylor, DK & Tiekink, ERT 2009, 'A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate', Journal of Organic Chemistry, vol. 74, no. 11, pp. 4400-4403. https://doi.org/10.1021/jo900392y

APA

Pedersen, D. S., Robinson, T. V., Taylor, D. K., & Tiekink, E. R. T. (2009). A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate. Journal of Organic Chemistry, 74(11), 4400-4403. https://doi.org/10.1021/jo900392y

Vancouver

Pedersen DS, Robinson TV, Taylor DK, Tiekink ERT. A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate. Journal of Organic Chemistry. 2009;74(11):4400-4403. https://doi.org/10.1021/jo900392y

Author

Pedersen, Daniel Sejer ; Robinson, Tony V ; Taylor, Dennis K ; Tiekink, Edward R T. / A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 11. pp. 4400-4403.

Bibtex

@article{e027ca306d3211de8bc9000ea68e967b,
title = "A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate",
abstract = "A series of 1,2-dioxanes 3 were ring-opened with Co(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2-C-d-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam.",
keywords = "Former Faculty of Pharmaceutical Sciences",
author = "Pedersen, {Daniel Sejer} and Robinson, {Tony V} and Taylor, {Dennis K} and Tiekink, {Edward R T}",
year = "2009",
doi = "10.1021/jo900392y",
language = "English",
volume = "74",
pages = "4400--4403",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "11",

}

RIS

TY - JOUR

T1 - A concise route to branched erythrono-gamma-lactones. Synthesis of the leaf-closing substance potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

AU - Pedersen, Daniel Sejer

AU - Robinson, Tony V

AU - Taylor, Dennis K

AU - Tiekink, Edward R T

PY - 2009

Y1 - 2009

N2 - A series of 1,2-dioxanes 3 were ring-opened with Co(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2-C-d-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam.

AB - A series of 1,2-dioxanes 3 were ring-opened with Co(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2-C-d-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam.

KW - Former Faculty of Pharmaceutical Sciences

U2 - 10.1021/jo900392y

DO - 10.1021/jo900392y

M3 - Journal article

C2 - 19402679

VL - 74

SP - 4400

EP - 4403

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 11

ER -

ID: 13087220