Stereocontrolled synthesis of the tetrahydrofuran unit of annonaceous acetogenins

被引：15

作者：

Li, KQ

Vig, S

Uckun, FM ^{[1
]}

机构：

[1] Wayne Hughes Inst, Drug Discovery Program, Roseville, MN 55113 USA

[2] Wayne Hughes Inst, Dept Chem, Roseville, MN 55113 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(98)00188-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The THF-epoxide 8 has been prepared from benzyl (R)-(-)-glycidyl ether using a 10-step synthetic scheme in a stereocontrolled fashion. Compound 8 is a highly useful synthon for the synthesis of mono-and di-THF acetogenins. This new synthetic approach can also be applied to the generation of large chemical libraries of acetogenins. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2063 / 2066

页数：4

共 21 条

[1] MODE OF ACTION OF BULLATACIN - A POTENT ANTITUMOR AND PESTICIDAL ANNONACEOUS ACETOGENIN
AHAMMADSAHIB, KI
HOLLINGWORTH, RM
MCGOVREN, JP
HUI, YH
MCLAUGHLIN, JL
[J]. LIFE SCIENCES, 1993, 53 (14) : 1113 - 1120
[2] APPROACH TO THE SYNTHESIS OF ANNONACEOUS ACETOGENINS FROM D-GLUCOSE
BERTRAND, P
GESSON, JP
[J]. TETRAHEDRON LETTERS, 1992, 33 (36) : 5177 - 5180
[3] ANNONACEOUS-ACETOGENINS - AN UPDATED REVIEW - APPENDIXES
FANG, XP
RIESER, MJ
GU, ZM
ZHAO, GX
MCLAUGHLIN, JL
[J]. PHYTOCHEMICAL ANALYSIS, 1993, 4 (02) : 49 - 67
[4] ANNONACEOUS ACETOGENINS - AN UPDATED REVIEW
FANG, XP
RIESER, MJ
GU, ZM
ZHAO, GX
MCLAUGHLIN, JL
[J]. PHYTOCHEMICAL ANALYSIS, 1993, 4 (01) : 27 - 48
[5] SYNTHESES OF ACETOGENINS OF ANNONACEAE - A NEW CLASS OF BIOACTIVE POLYKETIDES
FIGADERE, B
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) : 359 - 365
[6] FIGADERE B, 1997, J ORG CHEM, V62, P3248
[7] GU ZM, 1995, RECENT ADV PHYTOCHEM, V29, P249
[8] PROCEDURE FOR THE CATALYTIC ASYMMETRIC EPOXIDATION OF ALLYLIC ALCOHOLS IN THE PRESENCE OF MOLECULAR-SIEVES
HANSON, RM
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) : 1922 - 1925
[9] STEREOCONTROLLED SYNTHESIS OF 2,5-LINKED MONOTETRAHYDROFURAN UNITS OF ACETOGENINS
HARMANGE, JC
FIGADERE, B
CAVE, A
[J]. TETRAHEDRON LETTERS, 1992, 33 (39) : 5749 - 5752
[10] Highly efficient synthesis of the potent antitumor annonaceous acetogenin (+)-parviflorin
Hoye, TR
Ye, ZX
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (07) : 1801 - 1802

← 1 2 3 →