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
Éles, J
Kalaus, G
Lévai, A
Greiner, I
Kajtár-Peredy, M
Szabó, P
Szabó, L
Szántay, C
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (04) : 767 - 771
[5] BIOTRANSFORMATION OF TABERSONINE IN CELL-SUSPENSION CULTURES OF CATHARANTHUS-ROSEUS
FURUYA, T
SAKAMOTO, K
IIDA, K
ASADA, Y
YOSHIKAWA, T
SAKAI, SI
AIMI, N
[J]. PHYTOCHEMISTRY, 1992, 31 (09) : 3065 - 3068
[6] AN UNBOUNDED SYSTEMATIC SEARCH OF CONFORMATIONAL SPACE
GOODMAN, JM
STILL, WC
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1991, 12 (09) : 1110 - 1117
[7] ALKALOIDS FROM TABERNAEMONTANA-DIVARICATA
KAM, TS
ANURADHA, S
[J]. PHYTOCHEMISTRY, 1995, 40 (01) : 313 - 316
[8] KURT M, 1998, PHYTOCHEMISTRY, V49, P1457
[9] ALKALOID PRODUCTION IN CATHARANTHUS-ROSEUS CELL-CULTURES .4. CHARACTERIZATION OF THE 953 CELL-LINE
KURZ, WGW
CHATSON, KB
CONSTABEL, F
KUTNEY, JP
CHOI, LSL
KOLODZIEJCZYK, P
SLEIGH, SK
STUART, KL
WORTH, BR
[J]. HELVETICA CHIMICA ACTA, 1980, 63 (07) : 1891 - 1896
[10] TOTAL SYNTHESIS OF INDOLE AND DIHYDROINDOLE ALKALOIDS .1. INTRODUCTION AND TRANSANNULAR CYCLIZATION APPROACH
KUTNEY, JP
PIERS, E
BROWN, RT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (06) : 1700 - &

← 1 2 →