Synthetic studies on indoles and related compounds.: Part 46.: First total syntheses of 4,8-dioxygenated β-carboline alkaloids

被引：21

作者：

Suzuki, H ^{[1
]}

Unemoto, M ^{[1
]}

Hagiwara, M ^{[1
]}

Ohyama, T ^{[1
]}

Yokoyama, Y ^{[1
]}

Murakami, Y ^{[1
]}

机构：

[1] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 12期

关键词：

D O I：

10.1039/a900709a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total syntheses of naturally occurring 4,8-dioxygenated beta-carboline alkaloids 2a, 2d, 2g, and 2h are described. The synthetic route involves two methodologies that we developed; (i) an improved Fischer indolization for the synthesis of a 7-oxygenated indole using a tosyl group for protection of the phenolic group, (ii) construction of a 4-methoxy-beta-carboline skeleton by the C-3-selective cyclization of the C-2-substituent of the indole nucleus. The phenolic O-tosyl group of the beta-carboline skeleton was successfully cleaved to the phenol by Na-anthracenide, and this phenol was methylated with TMSCH2N2.

引用

页码：1717 / 1723

页数：7

共 7 条

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Osanai, K
Yokoyama, Y
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Murakami, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (11) : 1587 - 1590
[2] Synthetic studies on indoles and related compounds 44 -: Total synthesis of the structure proposed for picrasidine-H (dimeric 4-methoxy-β-carboline alkaloid)
Suzuki, H
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Yokoyama, Y
Murakami, Y
HETEROCYCLES, 1997, 46 : 57 - 60
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Suzuki, H
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Yokoyama, Y
Murakami, Y
HETEROCYCLES, 1996, 42 (01) : 83 - 86
[4] SYNTHETIC STUDIES ON TETRODOTOXIN AND RELATED COMPOUNDS .4. STEREOSPECIFIC TOTAL SYNTHESES OF DL-TETRODOTOXIN
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[5] Synthesis of vinca alkaloids and related compounds.: Part 108:: Efficient convergent synthetic pathway to the ibophyllidine skeleton IV.: First synthesis of (±)-18-hydroxy-20-epiibophyllidine
Toth, Florian
Kalaus, Gyoergy
Horvath, Vajk Daniel
Greiner, Istvan
Kajtar-Peredy, Maria
Goemoery, Agnes
Hazai, Laszlo
Szantay, Csaba
TETRAHEDRON, 2007, 63 (33) : 7823 - 7827
[6] Synthesis of vinca alkaloids and related compounds.: Part 107.: An efficient convergent synthetic pathway to build up the ibophyllidine skeleton III.: Total synthesis of (±)-ibophyllidine and (±)-20-epiibophyllidine
Toth, Florian
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Hazai, Laszlo
Szantay, Csaba
HETEROCYCLES, 2007, 71 (04) : 865 - 880
[7] Synthesis of vinca alkaloids and related compounds.: Part 106.: An efficient convergent synthetic pathway to build up the ibophyllidine skeleton II.: Total synthesis of (±)-deethylibophyllidine and (±)-14-epi-deethylibophyllidine
Toth, Florian
Kalaus, Gyorgy
Greiner, Istvan
Kajtar-Peredy, Maria
Gomory, Agnes
Hazai, Laszlo
Szantay, Csaba
HETEROCYCLES, 2006, 68 (11) : 2301 - 2317

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