CHIRAL SYNTHESIS OF POLYKETIDE-NATURAL PRODUCTS .40. TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC LYSOCELLIN .2. STEREOCONTROLLED SYNTHESIS OF THE C10-C23 FRAGMENT AND ITS ALDOL CONDENSATION WITH THE C1-C9 FRAGMENT TO COMPLETE THE TOTAL SYNTHESIS OF LYSOCELLIN

被引：6

作者：

HORITA, K ^{[1
]}

TANAKA, K ^{[1
]}

INOUE, T ^{[1
]}

YONEMITSU, O ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 38期

关键词：

POLYETHER ANTIBIOTIC; TOTAL SYNTHESIS; ALDOL REACTION; STEREOCONTROLLED SYNTHESIS;

D O I：

10.1016/S0040-4039(00)61140-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-10-C23 ethyl ketone (4) was synthesized via coupling of the C-16-C23 aldehyde (3) with the C-11-C-15 fragment (8), and subjected to the aldol reaction with the C1-C-9 aldehyde (2) to complete the first stereoselective total synthesis of the polyether antibiotic lysocellin (1).

引用

页码：5541 / 5544

页数：4

共 45 条

[41] TOTAL SYNTHESIS OF ERYTHRONOLIDE-B .2. SKELETON ASSEMBLY IN (C5-C9) + (C3-C4) + (C1-C2) + (C-11-C-13) SEQUENCE
SVIRIDOV, AF
ERMOLENKO, MS
YASHUNSKY, DV
BORODKIN, VS
KOCHETKOV, NK
TETRAHEDRON LETTERS, 1987, 28 (33) : 3839 - 3842
[42] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL PRODUCTS .47. SYNTHETIC STUDIES OF HALICHONDRIN-B, AN ANTITUMOR POLYETHER MACROLIDE ISOLATED FROM A MARINE SPONGE .2. EFFICIENT SYNTHESIS OF C16-C26 FRAGMENTS VIA CONSTRUCTION OF THE D-RING BY A HIGHLY STEREOCONTROLLED IODOETHERIFICATION
HORITA, K
NAGASAWA, M
HACHIYA, S
YONEMITSU, O
SYNLETT, 1994, (01) : 40 - 43
[43] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .21. SYNTHETIC STUDY OF (9S)-9-DIHYDROERYTHRONOLIDE A VIA WITTIG-HORNER COUPLING OF C1-C6 AND C7-C15 SEGMENTS
TONE, H
NISHI, T
OIKAWA, Y
HIKOTA, M
YONEMITSU, O
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (05) : 1160 - 1166
[44] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .20. ALTERNATIVE SYNTHESES OF THE C9-C15 AND C1-C5 SEGMENTS OF ERYTHRONOLIDE A VIA REGIO-SELECTIVE AND STEREO-SELECTIVE REDUCTIVE RING-OPENING OF 2,3-EPOXY ALCOHOLS
TONE, H
HIKOTA, M
HAMADA, T
NISHI, T
OIKAWA, Y
YONEMITSU, O
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (05) : 1155 - 1159
[45] CRYSTAL-STRUCTURE OF 1,2/5,6/9,10/13,14/17,18/21,22/25,26/29,30/33,34/37,38 DECABENZO-3,7,11,15,19,23,27,31,35,39-DECADEHYDRO[40]ANNULENE (C80H40, A 40-MEMBERED MACROCYCLIC RING AND THE SYNTHESIS AND CHARACTERIZATION OF ITS 80- (C160H80), 120- (C240H120), 160- (C-320)H-160) AND 200- (C400H200) MEMBERED RING HOMOLOGS
BALDWIN, KP
YOUNGS, WJ
SIMONS, RS
ROSE, J
ZIMMERMAN, P
HERCULES, DM
TESSIER, CA
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (10) : 1257 - 1258

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