APPROACH TO THE SYNTHESIS OF ANNONACEOUS ACETOGENINS FROM D-GLUCOSE

被引：17

作者：

BERTRAND, P ^{[1
]}

GESSON, JP ^{[1
]}

机构：

[1] CNRS,CHIM LAB 12,40 AVE RECTEUR PINEAU,F-86022 POITIERS,FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)79126-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation from D-glucose of threo-trans-threo and threo-cis-threo synthons 12 and 13 of the monochiral synthesis of mono (or eventually bis) tetrahydrofuran acetogenins is described. Their structure have been proven by degradation and comparison with a racemic sample of a threo-cis-threo aldehyde prepared by permanganate oxidation of the corresponding diene.

引用

页码：5177 / 5180

页数：4

共 18 条

[1] THE RELATIVE CONFIGURATION OF ACETOGENINS ISOLATED FROM ANNONA-SQUAMOSA - ANNONIN-I (SQUAMOCIN) AND ANNONIN-VI
BORN, L
LIEB, F
LORENTZEN, JP
MOESCHLER, H
NONFON, M
SOLLNER, R
WENDISCH, D
[J]. PLANTA MEDICA, 1990, 56 (03) : 312 - 316
[2] FREUDENBERG K, 1928, CHEM BER, V61, P1735
[3] THE TOTAL SYNTHESIS OF (+)-IONOMYCIN
HANESSIAN, S
COOKE, NG
DEHOFF, B
SAKITO, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) : 5276 - 5290
[4] TOTAL SYNTHESIS OF THE MESO-TRITERPENE POLYETHER TEURILENE
HASHIMOTO, M
HARIGAYA, H
YANAGIYA, M
SHIRAHAMA, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) : 2299 - 2311
[5] SYNTHESIS OF (+)-(15,16,19,20,23,24)-HEXEPI-UVARICIN - A BIS(TETRAHYDROFURANYL) ANNONACEOUS ACETOGENIN ANALOG
HOYE, TR
HANSON, PR
KOVELESKY, AC
OCAIN, TD
ZHUANG, ZP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9369 - 9371
[6] SYMMETRY-ASSISTED SYNTHESIS OF TRIEPOXIDE STEREOISOMERS OF (E,Z,E)-DODECA-2,6,10-TRIENE-1,12-DIOL AND THEIR CASCADE REACTIONS TO 2,5-LINKED BISTETRAHYDROFURANS
HOYE, TR
SUHADOLNIK, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) : 5312 - 5313
[7] STEREOCONTROLLED SYNTHESIS OF 2,5-LINKED BISTETRAHYDROFURANS VIA THE TRIEPOXIDE CASCADE REACTION
HOYE, TR
SUHADOLNIK, JC
[J]. TETRAHEDRON, 1986, 42 (11) : 2855 - 2862
[8] Inch T. D., 1967, CARBOHYD RES, V5, P45
[9] JOLAD SD, 1982, J ORG CHEM, V47, P3151
[10] DIE PERMANGANATOXYDATION VON 1,5-DIENVERBINDUNGEN
KLEIN, E
ROJAHN, W
[J]. TETRAHEDRON, 1965, 21 (09) : 2353 - &

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