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

引用

收藏

页码：2463 / 2466

页数：4

相关论文

共 23 条

[1] C-NUCLEOSIDE STUDIES .13. A NEW SYNTHESIS OF 2,3,5-TRI-OMICRON-BENZYL-ALPHA(AND 2,3,5-TRI-OMICRON-BENZYL-BETA)-D-RIBOFURANOSYLETHYNE INVOLVING BENZYLOXY PARTICIPATION, AND A SYNTHESIS OF ALPHA-SHOWDOMYCIN [J].

ASLANISHOTORBANI, G ;

BUCHANAN, JG ;

EDGAR, AR ;

SHANKS, CT ;

WILLIAMS, GC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (08) :2267-2272

[2] THE USE OF TRIPHENYLPHOSPHINE DIETHYL AZODICARBOXYLATE (DEAD) FOR THE CYCLIZATION OF 1,4-AMINO AND 1,5-AMINO ALCOHOLS [J].

BERNOTAS, RC ;

CUBE, RV .

TETRAHEDRON LETTERS, 1991, 32 (02) :161-164

[3] CARBON ACIDS .9. EFFECTS OF DIVALENT SULFUR AND DIVALENT OXYGEN ON CARBANION STABILITIES [J].

BORDWELL, FG ;

VANDERPUY, M ;

VANIER, NR .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (10) :1885-1886

[4]

CARLOCK JT, 1978, TETRAHEDRON LETT, P5153

[5]

CASINOVI CG, 1962, GAZZ CHIM ITAL, V92, P479

[6] TOTAL ASYMMETRIC SYNTHESES OF 1,5-DIDEOXY-1,5-IMINOOCTITOLS AND 1,2,6,7,8-PENTAHYDROXYINDOLIZIDINES [J].

CHEN, YW ;

VOGEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2487-2496

[7] PREPARATION AND SCOPE OF A REMARKABLY ROBUST PRIMARY ALCOHOL PROTECTIVE GROUP [J].

CHO, HS ;

YU, JR ;

FALCK, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) :8354-8355

[8] ENANTIOSELECTIVE SYNTHESIS OF 3-AZABICYCLO[4.3.0]NONANE ALKALOIDS [J].

CID, MM ;

POMBOVILLAR, E .

HELVETICA CHIMICA ACTA, 1993, 76 (04) :1591-1607

[9]

Falck J. R., 1994, Tetrahedron Letters, V35, P5997, DOI 10.1016/0040-4039(94)88058-1

[10] SYNTHETIC AND STEREOCHEMICAL STUDIES OF THE OCTAHYDRO-1-BENZOPYRAN SYSTEM [J].

GRIFFITHS, DV ;

WILCOX, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (04) :431-436