Anodic coupling reactions: Probing the stereochemistry of tetrahydrofuran formation. A short, convenient synthesis of linalool oxide

被引：31

作者：

Duan, SQ ^{[1
]}

Moeller, KD ^{[1
]}

机构：

[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 17期

关键词：

D O I：

10.1021/ol0162670

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Intramolecular coupling reactions between enol ether radical cations and oxygen nucleophiles are primarily governed by stereoelectronics. By taking advantage of this observation, a tetrahydrofuran building block for use in constructing (+)-linalool oxide and rotundisine has been synthesized in four steps from a commercially available starting material. The synthesis of (+)-linalool oxide has been completed.

引用

收藏

页码：2685 / 2688

页数：4

相关论文

共 17 条

[1]

BRIMBLE MA, 1995, SYNTHESIS-STUTTGART, P1263

[2] FROM CRYSTAL STATICS TO CHEMICAL-DYNAMICS [J].

BURGI, HB ;

DUNITZ, JD .

ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (05) :153-161

[3] GEOMETRICAL REACTION COORDINATES .2. NUCLEOPHILIC ADDITION TO A CARBONYL GROUP [J].

BURGI, HB ;

DUNITZ, JD ;

SHEFTER, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :5065-5067

[4] LARGE-PORE BIFUNCTIONAL TITANIUM-ALUMINOSILICATES - THE INORGANIC NONENZYMATIC VERSION OF THE EPOXIDASE CONVERSION OF LINALOOL TO CYCLIC ETHERS [J].

CORMA, A ;

IGLESIAS, M ;

SANCHEZ, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (16) :1635-1636

[5]

DESLONGCHAMPS P, 1983, STEREOELECTRONIC EFF, P32

[6] Palladium(0)-catalysed synthesis of cis- and trans-linalyl oxides [J].

FournierNguefack, C ;

Lhoste, P ;

Sinou, D .

TETRAHEDRON, 1997, 53 (12) :4353-4362

[7] Anodic electrochemistry and the use of a 6-volt lantern battery: A simple method for attempting electrochemically based synthetic transformations [J].

Frey, DA ;

Wu, N ;

Moeller, KD .

TETRAHEDRON LETTERS, 1996, 37 (46) :8317-8320

[8]

GARCIA MA, 1994, SYNLETT, P911

[9] Pigments of fungi (Macromycetes) [J].

Gill, M .

NATURAL PRODUCT REPORTS, 1999, 16 (03) :301-317

[10] REGIOSELECTIVE HYDROXYLATIONS OF 1,3-DIENES VIA HYDROCOBALTATION REACTIONS - FACILE CONVERSION OF MYRCENE TO GERANIOL AND TO (+/-)-LINALOOL [J].

HOWELL, AR ;

PATTENDEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (02) :103-104