CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .32. SYNTHESIS OF ERYTHRONOLIDE A VIA A VERY EFFICIENT MACROLACTONIZATION UNDER USUAL ACYLATION CONDITIONS WITH THE YAMAGUCHI REAGENT

被引：144

作者：

HIKOTA, M ^{[1
]}

SAKURAI, Y ^{[1
]}

HORITA, K ^{[1
]}

YONEMITSU, O ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 44期

关键词：

D O I：

10.1016/S0040-4039(00)97066-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Macrolactonization of 3,5-O-(3,4-dimethoxybenzylidene)-9,11-O-(2,4,6-trimethylbenzylidene)(9S)-9-dihydroerythronolide A seco-acid (4) was reexamined under various conditions and found to proceed rapidly only by treatment of 4 with Yamaguchi's reagent, 2,4,6-trichlorobenzoyl chloride, in the presence of a large excess of TEA and a small amount of DMAP at room temperature to give the corresponding 14-membered erythronolide A derivative (7) in almost quantitative yield. © 1990.

引用

页码：6367 / 6370

页数：4

共 19 条

[1] PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION
BODEN, EP
KECK, GE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) : 2394 - 2395
[2] COREY EJ, 1976, TETRAHEDRON LETT, P3405
[3] EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES
COREY, EJ
NICOLAOU, KC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) : 5614 - 5616
[4] CHIRAL SYNTHESIS OF POLYKETIDE DERIVED NATURAL-PRODUCTS .27. STEREOSELECTIVE SYNTHESIS OF ERYTHRONOLIDE-A VIA AN EXTREMELY EFFICIENT MACROLACTONIZATION BY THE MODIFIED YAMAGUCHI METHOD
HIKOTA, M
TONE, H
HORITA, K
YONEMITSU, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 7 - 9
[5] HIKOTA M, IN PRESS TETRAHEDRON
[6] 4-DIALKYLAMINOPYRIDINES AS ACYLATION CATALYSTS .4. 4-DIALKYLAMINOPYRIDINES AS HIGHLY ACTIVE ACYLATION CATALYSTS
HOFLE, G
STEGLICH, W
VORBRUGGEN, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (08): : 569 - &
[7] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION
INANAGA, J
HIRATA, K
SAEKI, H
KATSUKI, T
YAMAGUCHI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) : 1989 - 1993
[8] STUDIES ON POLYNUCLEOTIDES .30. COMPARATIVE STUDY OF REAGENTS FOR SYNTHESIS OF C3]-C5] INTERNUCLEOTIDIC LINKAGE
JACOB, TM
KHORANA, HG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (08) : 1630 - &
[9] TOTAL SYNTHESIS OF (+)-COLLETODIOL - NEW METHODOLOGY FOR THE SYNTHESIS OF MACROLACTONES
KECK, GE
BODEN, EP
WILEY, MR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) : 896 - 906
[10] SYNTHETIC STUDIES OF ERYTHROMYCINS .3. TOTAL SYNTHESIS OF ERYTHRONOLIDE-A THROUGH (9S)-9-DIHYDROERYTHRONOLIDE-A
KINOSHITA, M
ARAI, M
OHSAWA, N
NAKATA, M
[J]. TETRAHEDRON LETTERS, 1986, 27 (16) : 1815 - 1818

← 1 2 →