Synthesis of vinca alkaloids and related compounds.: 100.: Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system.: First synthesis of some alkaloids containing the epoxy ring

被引：18

作者：

Éles, J

Kalaus, G

Greiner, I

Kajtár-Peredy, M

Szabó, P

Keserû, GM

Szabó, L

Szántay, C

机构：

[1] Budapest Univ Technol & Econ, Dept Organ Chem, H-1111 Budapest, Hungary

[2] Gedeon Richter Chem Works Ltd, Chem Works, H-1103 Budapest, Hungary

[3] Hungarian Acad Sci, Chem Res Ctr, Inst Chem, H-1025 Budapest, Hungary

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 21期

关键词：

D O I：

10.1021/jo020386r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first syntheses of the alkaloids (-)-mehranine (3), (+)-voaphylline/conoflorine (4), (+)-N-a-methylvoaphylline/hecubine (5), and (-)-lochnericine (2) were achieved by stereoselective epoxidation starting from (-)-tabersonine (1), through intermediates with the aspidospermane and quebrachamine skeleton.

引用

页码：7255 / 7260

页数：6

共 15 条

[1]

AIMI N, 1978, CHEM PHARM BULL, V26, P1182, DOI 10.1248/cpb.26.1182

[2]

ATTAURRAHMAN, 1983, Z NATURFORSCH B, V38, P117

[3]

CSOKASI, UNPUB

[4] Synthesis of vinca alakaloids and related compounds 98.: Oxidation with dimethyldioxirane of compounds containing the aspidospermane and quebrachamine ring system.: A simple synthesis of (7S,20S)-(+)-rhazidigenine and (2R,7S,20S)-(+)-rhazidine [J].