Mixed metal base LICKOR as key reagent in the synthesis of conjugate alkadien-1-ols. A new route to an insect attractant

被引：7

作者：

Cominetti, F ^{[1
]}

Deagostino, A ^{[1
]}

Prandi, C ^{[1
]}

Venturello, P ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Chim Gen & Organ Applicata, I-10125 Turin, Italy

来源：

TETRAHEDRON | 1998年 / 54卷 / 48期

关键词：

D O I：

10.1016/S0040-4020(98)00918-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrahydrofurfuryl alcohol has been oxidized to the corresponding aldehyde (1) using TPAP and NMO. Subsequent Wittig reaction afforded 2-alk-1-enyltetrahydrofurans (2 and 3) that on be metalated with Schlosser's reagent LICKOR. The base promotes the 1,4-eliminative ring fission, affording conjugate alkadien-1-ols (4 and 5) with high all E stereoselectivity. In the case of 2-pent-1-enyltetrahydrofuran, elimination reaction gives (4E, 6E)-nona-4,6-dien-1-ol (5), which is structurally related to two sex pheromone components of the Caribbean fruit ny, Anastrepha suspensa. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：14603 / 14608

页数：6

共 28 条

[1] SYNTHESIS OF POLYCYCLIC POLYETHERS .1. STEREOSELECTIVITY OF THE HETEROCYCLIZATION OF GAMMA-DELTA-ETHYLENE TETRAHYDROFURFURYLIC ALCOHOLS WITH MERCURIC-SALTS [J].

AMOUROUX, R ;

CHASTRETTE, F ;

CHASTRETTE, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (03) :565-569

[2] APPROACHES TO CYTOCHALASAN SYNTHESIS - MACROCYCLE FORMATION USING AN INTRA-MOLECULAR DIELS-ALDER REACTION [J].

BAILEY, SJ ;

THOMAS, EJ ;

TURNER, WB ;

JARVIS, JAJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (11) :474-475

[3] FACILE SN' REACTION OF ALKYL-LITHIUMS WITH 2-VINYL-1,3-DIOXANE [J].

BAILEY, WF ;

ZARTUN, DL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (01) :34-35

[4]

BASKARAN S, 1992, J CHEM RES-S, P290

[5]

BASKARAN S, 1992, J CHEM RES M, P2213

[6] TOTAL SYNTHESIS OF DL-CERULENIN [J].

BOECKMAN, RK ;

THOMAS, EW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (04) :987-994

[7]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[8] Intramolecular Diels-Alder reaction of functionalized trienes: synthesis of medium-ring lactones [J].

Deagostino, A ;

Maddaluno, J ;

Mella, M ;

Prandi, C ;

Venturello, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (05) :881-888

[9] Reaction of alpha,beta-unsaturated and alpha-phenyl acetals with epoxides, promoted by lithium-potassium mixed base LICKOR: Synthesis of homoallyl alcohols [J].

Deagostino, A ;

Prandi, C ;

Venturello, P .

TETRAHEDRON, 1996, 52 (04) :1433-1442

[10] Synthesis of functionalized trienes and regioselective formation of medium-ring lactones through intramolecular Diels-Alder reaction [J].

Deagostino, A ;

Maddaluno, J ;

Prandi, C ;

Venturello, P .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7597-7599

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