Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-alpha-skytanthine

被引：74

作者：

Tsunoda, T

Ozaki, F

Shirakata, N

Tamaoka, Y

Yamamoto, H

Ito, S

机构：

[1] Faculty of Pharmaceutical Sciences, Tokushima Bunri University

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 14期

关键词：

D O I：

10.1016/0040-4039(96)00319-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyanomethylenetributylphosphorane was shown to mediate the dehydrocyclization of diols and amino alcohols to give the corresponding 6-membered O- and N-heterocycles in 90% or better yields. Using the reaction as a key step, (+)-alpha-skytanthine, a unique mono terpene alkaloid was synthesized stereoselectively. Copyright (C) 1996 Elsevier Science Ltd

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页码：2463 / 2466

页数：4

相关论文

共 23 条

[11] STEREOSELECTIVE SYNTHESIS OF THE C-4 LINKED IMIDAZOLE NUCLEOSIDES USING MODIFIED MITSUNOBU REACTION [J].

HARUSAWA, S ;

MURAI, Y ;

MORIYAMA, H ;

OHISHI, H ;

YONEDA, R ;

KURIHARA, T .

TETRAHEDRON LETTERS, 1995, 36 (18) :3165-3168

[12]

Hughes D.L., 1992, ORG REACT, V42, P335, DOI [10.1002/0471264180.OR042.02, DOI 10.1002/0471264180.OR042.02]

[13] APPLICATION OF THE AZA-CLAISEN REARRANGEMENT TO THE TOTAL SYNTHESIS OF NATURAL-PRODUCTS - (-)-ISOIRIDOMYRMECIN [J].

ITO, S ;

TSUNODA, T .

PURE AND APPLIED CHEMISTRY, 1994, 66 (10-11) :2071-2074

[14] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[15] STEREOCHEMICAL AND REGIOCHEMICAL ASPECTS OF THE MITSUNOBU REACTION IN SYNTHESIS OF CHIRAL AMINO ETHER LIGANDS FOR ASYMMETRIC REACTIONS [J].

OKUDA, M ;

TOMIOKA, K .

TETRAHEDRON LETTERS, 1994, 35 (26) :4585-4586

[16] ENANTIOSELECTIVE SYNTHESES OF (+)-ALPHA-SKYTANTHINE, (+)-DELTA-SKYTANTHINE AND (+)-IRIDOMYRMECIN BY AN INTRAMOLECULAR MAGNESIUM-ENE REACTION [J].

OPPOLZER, W ;

JACOBSEN, EJ .

TETRAHEDRON LETTERS, 1986, 27 (10) :1141-1144

[17] SOLID-PHASE SYNTHESIS OF ARYL ETHERS VIA THE MITSUNOBU REACTION [J].

RANO, TA ;

CHAPMAN, KT .

TETRAHEDRON LETTERS, 1995, 36 (22) :3789-3792

[18] FIRST-SYNTHESIS OF THE NOVEL GELSEMIUM ALKALOIDS, GELSELEGINE, GELSENICINE, AND GELSEDINE USING A BIOMIMETIC APPROACH [J].

TAKAYAMA, H ;

TOMINAGA, Y ;

KITAJIMA, M ;

AIMI, N ;

SAKAI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4381-4385

[19] NOVEL REACTIVITY OF STABILIZED METHYLENETRIBUTYLPHOSPHORANE - A NEW MITSUNOBU REAGENT [J].

TSUNODA, T ;

OZAKI, F ;

ITO, S .

TETRAHEDRON LETTERS, 1994, 35 (28) :5081-5082

[20] N,N,N',N'-TETRAMETHYLAZODICARBOXAMIDE (TMAD), A NEW VERSATILE REAGENT FOR MITSUNOBU REACTION - ITS APPLICATION TO SYNTHESIS OF SECONDARY-AMINES [J].

TSUNODA, T ;

OTSUKA, J ;

YAMAMIYA, Y ;

ITO, S .

CHEMISTRY LETTERS, 1994, (03) :539-542