Solid-phase selenium-catalyzed selective allylic chlorination of polyprenoids:: Facile syntheses of biologically active terpenoids

被引：35

作者：

Barrero, Alejandro F.

Quilez del Moral, Jose F.

Mar Herrador, M.

Cortes, Manuel

Arteaga, Pilar

Catalan, Julieta V.

Sanchez, Elena M.

Arteaga, Jesus F.

机构：

[1] Univ Granada, Inst Biotechnol, Dept Organ Chem, E-18071 Granada, Spain

[2] Pontificia Univ Catolica Chile, Fac Quim, Santiago, Chile

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 15期

关键词：

D O I：

10.1021/jo060760d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective halogenation of the terminal isopropylidene unit of different acyclic polyolefinic polyprenoids (farnesyl acetate, geranylgeranyl acetate, squalene, etc.) using NCS/ catalytic polymer-supported selenenyl bromide is described; good to excellent yields are obtained (68-96%). The first applications of this protocol include the concise synthesis of bioactive terpenoids 1-3.

引用

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页码：5811 / 5814

页数：4

相关论文

共 30 条

[1] A convenient synthesis of A-ring-functionalized podolactones. Revision of the structure of wentilactone B [J].

Barrero, AF ;

Herrador, MM ;

del Moral, JFQ ;

Valdivia, MV .

ORGANIC LETTERS, 2002, 4 (08) :1379-1382

[2] A new strategy for the synthesis of cyclic terpenoids based on the radical opening of acyclic epoxypolyenes [J].

Barrero, AF ;

Cuerva, JM ;

Herrador, MM ;

Valdivia, MV .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :4074-4078

[3] A linear sesterterpene, two squalene derivatives and two peptide derivatives from Croton hieronymi [J].

Catalán, CAN ;

de Heluani, CS ;

Kotowicz, C ;

Gedris, TE ;

Herz, W .

PHYTOCHEMISTRY, 2003, 64 (02) :625-629

[4]

Corey E.J., 1989, The Logic of Chemical Synthesis

[5] SHORT ENANTIOSELECTIVE SYNTHESIS OF (-)-OVALICIN, A POTENT INHIBITOR OF ANGIOGENESIS, USING SUBSTRATE-ENHANCED CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

COREY, EJ ;

GUZMANPEREZ, A ;

NOE, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12109-12110

[6] A MECHANISTICALLY DESIGNED BIS-CINCHONA ALKALOID LIGAND ALLOWS POSITION-SELECTIVE AND ENANTIOSELECTIVE DIHYDROXYLATION OF FARNESOL AND OTHER OLIGOPRENYL DERIVATIVES AT THE TERMINAL ISOPROPYLIDENE UNIT [J].

COREY, EJ ;

NOE, MC ;

LIN, SZ .

TETRAHEDRON LETTERS, 1995, 36 (48) :8741-8744

[7] Highly effective transition structure designed catalyst for the enantio- and position-selective dihydroxylation of polyisoprenoids [J].

Corey, EJ ;

Zhang, JH .

ORGANIC LETTERS, 2001, 3 (20) :3211-3214

[8]

COX NJG, 1992, J CHEM SOC P1, V11, P1313

[9] ASYMMETRIC DIHYDROXYLATION OF SQUALENE [J].

CRISPINO, GA ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1992, 33 (30) :4273-4274

[10] ω-Hydroxylation of farnesol by mammalian cytochromes P450 [J].

DeBarber, AE ;

Bleyle, LA ;

Roullet, JBO ;

Koop, DR .

BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS, 2004, 1682 (1-3) :18-27