New total synthesis of (+/-)-chuangxinmycin

被引：23

作者：

Kato, K ^{[1
]}

Ono, M ^{[1
]}

Akita, H ^{[1
]}

机构：

[1] TOHO UNIV,SCH PHARMACEUT SCI,FUNABASHI,CHIBA 274,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(97)00174-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-4'-Iodoindolmycenate 6 was stereoselectively converted into the (+/-)-(2,3)-syn-2-thioacerocy ester 16 with retention of C-2-stereochemistry in (+/-)-6. Palladium-catalysed cyclisation of indolyl iodide and the internal C-2 thiol group of the substrate (+/-)-17 derived from (+/-)-16 gave the (+/-)-cis methyl ester 2 of natural chuangxinmycin (1). (C) 1997 Elsevier Science Ltd.

引用

页码：1805 / 1808

页数：4

共 18 条

[1] FORMAL TOTAL SYNTHESIS OF (-)-INDOLMYCIN
AKITA, H
KAWAGUCHI, T
ENOKI, Y
OISHI, T
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (02) : 323 - 328
[2] SYNTHESIS OF INDOLES VIA RING-CLOSURE OF 2-ALKYLNITROANILINE DERIVATIVES
BERGMAN, J
SAND, P
[J]. TETRAHEDRON, 1990, 46 (17) : 6085 - 6112
[3] ABSOLUTE CONFIGURATION OF INDOLMYCIN
CHAN, TH
HILL, RK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) : 3519 - &
[4] Chang C.-P., 1976, HUA HSUEH HSUEH PAO, V34, P133
[5] *CHIN AC MED SCI I, 1977, SCI SINICA, V20, P106
[6] GU ZP, 1985, ACTA CHIM SINICA, V43, P250
[7] Guo X L, 1987, Yao Xue Xue Bao, V22, P671
[8] A NEW, GENERAL ENTRY TO 4-SUBSTITUTED INDOLES - SYNTHESIS OF (S)-(-)-PINDOLOL AND (+/-)-CHUANGXINMYCIN
ISHIBASHI, H
TABATA, T
HANAOKA, K
IRIYAMA, H
AKAMATSU, S
IKEDA, M
[J]. TETRAHEDRON LETTERS, 1993, 34 (03) : 489 - 492
[9] TOTAL SYNTHESIS OF THE UNIQUE INDOLE ALKALOID CHUANGXINMYCIN - APPLICATION OF NITRO-GROUP DISPLACEMENT-REACTIONS IN ORGANIC-SYNTHESIS
KOZIKOWSKI, AP
GRECO, MN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) : 1165 - 1166
[10] SYNTHETIC STUDIES IN THE INDOLE SERIES - PREPARATION OF THE UNIQUE ANTIBIOTIC ALKALOID CHUANGXINMYCIN BY A NITRO-GROUP DISPLACEMENT REACTION
KOZIKOWSKI, AP
GRECO, MN
SPRINGER, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (26) : 7622 - 7626

← 1 2 →