Regio- and stereoselective synthesis of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran from accessible labdane diterpenoids (+)-larixol and (-)-sclareol

P.E. Vlad; A. Ciocarlan; C. Edu; A. Aricu; A. Biriiac; M. Coltsa; M. D'Ambrosio; C. Deleanu; A. Nicolescu; S. Shova; N. Vornicu; Æ. de Groot

doi:10.1016/j.tet.2012.10.096

Regio- and stereoselective synthesis of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran from accessible labdane diterpenoids (+)-larixol and (-)-sclareol

P.E. Vlad, A. Ciocarlan, C. Edu, A. Aricu, A. Biriiac, M. Coltsa, M. D'Ambrosio, C. Deleanu, A. Nicolescu, S. Shova, N. Vornicu, Æ. de Groot

Organic Chemistry

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

18 Citations (Scopus)

Abstract

Starting from (+)-larixol and (-)-sclareol, new syntheses of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran have been elaborated in high yields. (+)-6-Ketowinterin was synthesized for the first time. Both euryfurans are excellent starting materials for the synthesis of important polyfunctional biologically active drimanic compounds. (C) 2012 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	918-926
Journal	Tetrahedron
Volume	69
Issue number	2
DOIs	https://doi.org/10.1016/j.tet.2012.10.096
Publication status	Published - 2013

Keywords

drimane-related sesquiterpenes
ring transfer-reaction
efficient synthesis
singlet oxygen
(+/-)-euryfuran
derivatives
euryfuran
sponge
(&/-)-isodrimenin
photooxygenation

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Vlad, P. E., Ciocarlan, A., Edu, C., Aricu, A., Biriiac, A., Coltsa, M., D'Ambrosio, M., Deleanu, C., Nicolescu, A., Shova, S., Vornicu, N., & de Groot, Æ. (2013). Regio- and stereoselective synthesis of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran from accessible labdane diterpenoids (+)-larixol and (-)-sclareol. Tetrahedron, 69(2), 918-926. https://doi.org/10.1016/j.tet.2012.10.096

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title = "Regio- and stereoselective synthesis of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran from accessible labdane diterpenoids (+)-larixol and (-)-sclareol",

abstract = "Starting from (+)-larixol and (-)-sclareol, new syntheses of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran have been elaborated in high yields. (+)-6-Ketowinterin was synthesized for the first time. Both euryfurans are excellent starting materials for the synthesis of important polyfunctional biologically active drimanic compounds. (C) 2012 Elsevier Ltd. All rights reserved.",

keywords = "drimane-related sesquiterpenes, ring transfer-reaction, efficient synthesis, singlet oxygen, (+/-)-euryfuran, derivatives, euryfuran, sponge, (&/-)-isodrimenin, photooxygenation",

author = "P.E. Vlad and A. Ciocarlan and C. Edu and A. Aricu and A. Biriiac and M. Coltsa and M. D'Ambrosio and C. Deleanu and A. Nicolescu and S. Shova and N. Vornicu and {de Groot}, {\AE}.",

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volume = "69",

pages = "918--926",

journal = "Tetrahedron",

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Vlad, PE, Ciocarlan, A, Edu, C, Aricu, A, Biriiac, A, Coltsa, M, D'Ambrosio, M, Deleanu, C, Nicolescu, A, Shova, S, Vornicu, N & de Groot, Æ 2013, 'Regio- and stereoselective synthesis of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran from accessible labdane diterpenoids (+)-larixol and (-)-sclareol', Tetrahedron, vol. 69, no. 2, pp. 918-926. https://doi.org/10.1016/j.tet.2012.10.096

TY - JOUR

T1 - Regio- and stereoselective synthesis of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran from accessible labdane diterpenoids (+)-larixol and (-)-sclareol

AU - Vlad, P.E.

AU - Ciocarlan, A.

AU - Edu, C.

AU - Aricu, A.

AU - Biriiac, A.

AU - Coltsa, M.

AU - D'Ambrosio, M.

AU - Deleanu, C.

AU - Nicolescu, A.

AU - Shova, S.

AU - Vornicu, N.

AU - de Groot, Æ.

N1 - WOS:000314371800068

PY - 2013

Y1 - 2013

N2 - Starting from (+)-larixol and (-)-sclareol, new syntheses of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran have been elaborated in high yields. (+)-6-Ketowinterin was synthesized for the first time. Both euryfurans are excellent starting materials for the synthesis of important polyfunctional biologically active drimanic compounds. (C) 2012 Elsevier Ltd. All rights reserved.

AB - Starting from (+)-larixol and (-)-sclareol, new syntheses of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran have been elaborated in high yields. (+)-6-Ketowinterin was synthesized for the first time. Both euryfurans are excellent starting materials for the synthesis of important polyfunctional biologically active drimanic compounds. (C) 2012 Elsevier Ltd. All rights reserved.

KW - drimane-related sesquiterpenes

KW - ring transfer-reaction

KW - efficient synthesis

KW - singlet oxygen

KW - (+/-)-euryfuran

KW - derivatives

KW - euryfuran

KW - sponge

KW - (&/-)-isodrimenin

KW - photooxygenation

U2 - 10.1016/j.tet.2012.10.096

DO - 10.1016/j.tet.2012.10.096

M3 - Article

SN - 0040-4020

VL - 69

SP - 918

EP - 926

JO - Tetrahedron

JF - Tetrahedron

IS - 2

ER -

Regio- and stereoselective synthesis of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (-)-7-ketoeuryfuran from accessible labdane diterpenoids (+)-larixol and (-)-sclareol

Abstract

Keywords

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