Synthesis of (+)-perillyl alcohol from (+)-limonene

被引：22

作者：

Geoghegan, Kimberly ^{[1
]}

Evans, Paul ^{[1
]}

机构：

[1] Univ Coll Dublin, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 08期

关键词：

Monoterpene; Isomerisation; pi-Allyl palladium complex; Overman rearrangement; FORMAL SYNTHESIS; PALLADIUM; ACETATES; CIS-2-CYCLOPENTENE-1,4-DIOLS; ISOMERIZATION; LIMONENE; ROUTE;

D O I：

10.1016/j.tetlet.2014.01.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Perillyl alcohol (1) has been synthesised in four steps and 39% overall yield from commercially available limonene oxide (4). The sequence features, as its key step, a palladium(0)-mediated transformation of a secondary allylic acetate (6) into its primary isomer (7). An application of (+)-perillyl alcohol (1) in a formal synthesis of naturally occurring (-)-mesembrine (2) and (-)-mesembranol was demonstrated. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1431 / 1433

页数：3

共 19 条

[1] Concise Total Synthesis of Spirocurcasone [J].

Abe, Hideki ;

Sato, Akimi ;

Kobayashi, Toyoharu ;

Ito, Hisanaka .

ORGANIC LETTERS, 2013, 15 (06) :1298-1301

[2] Biogenetic-type synthesis of (+)-cymbodiacetal, a constituent of Cymbopogon martinii [J].

D'Souza, AM ;

Paknikar, SK ;

Dev, V ;

Beauchamp, PS ;

Kamat, SP .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (04) :700-702

[3] PALLADIUM-CATALYZED SYN 1,4-ADDITIONS OF SILYL-DERIVED CARBOXYLATES AND PHENOXIDES TO CYCLOPENTADIENE MONOEPOXIDE - A STEREOCONTROLLED AND REGIOCONTROLLED ROUTE TO DIFFERENTIALLY PROTECTED CIS-2-CYCLOPENTENE-1,4-DIOLS [J].

DEARDORFF, DR ;

SHAMBAYATI, S ;

LINDE, RG ;

DUNN, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :189-191

[4] A PALLADIUM-CATALYZED ROUTE TO MONOPROTECTED AND DIPROTECTED CIS-2-CYCLOPENTENE-1,4-DIOLS [J].

DEARDORFF, DR ;

MYLES, DC ;

MACFERRIN, KD .

TETRAHEDRON LETTERS, 1985, 26 (46) :5615-5618

[5] Synthesis of (-)-(Z)-deoxypukalide [J].

Donohoe, Timothy J. ;

Ironmonger, Alan ;

Kershaw, Neil M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (38) :7314-7316

[6] An efficient and convenient synthesis of enantiopure 4-(t-butyldimethylsilyloxy)-cyclohex-2-en-1-one:: a formal synthesis of (±)-mesembranol [J].

Evarts, JB ;

Fuchs, PL .

TETRAHEDRON LETTERS, 2001, 42 (22) :3673-3675

[7] Double Reduction of Cyclic Aromatic Sulfonamides: Synthesis of (+)-Mesembrine and (+)-Mesembranol [J].

Geoghegan, Kimberly ;

Evans, Paul .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) :3410-3415

[8] COMPLETE TRANSFER OF CHIRALITY IN THE [3,3]-SIGMATROPIC REARRANGEMENT OF ALLYLIC ACETATES CATALYZED BY PALLADIUM(II) - APPLICATION TO STEREOCONTROLLED SYNTHESES OF PROSTAGLANDINS POSSESSING EITHER THE C-15(S) OR C-15(R) CONFIGURATIO [J].

GRIECO, PA ;

TAKIGAWA, T ;

BONGERS, SL ;

TANAKA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) :7587-7588

[9] Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors [J].

Hanus, LO ;

Tchilibon, S ;

Ponde, DE ;

Breuer, A ;

Fride, E ;

Mechoulam, R .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (06) :1116-1123

[10]

JOgensen L, 2013, SCIENCE, V341, P878

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