ENANTIOCONTROLLED TOTAL SYNTHESES OF (-)-PHYSOVENINE AND (-)-PHYSOSTIGMINE

被引：78

作者：

TAKANO, S

MORIYA, M

OGASAWARA, K

机构：

[1] Pharmaceutical Institute, Tohoku University, Aobayama

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 21期

关键词：

D O I：

10.1021/jo00021a006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiocontrolled total syntheses of the Calabar bean alkaloid (-)-physovenine (1) and (-)-physostigmine (2) have been achieved in a concise manner starting from the optically active tricyclic enone 3 employing a Fischer indolization reaction under nonacidic conditions as the key step.

引用

页码：5982 / 5984

页数：3

共 14 条

[1] BIOACTIVE ALKALOIDS .4. RESULTS OF RECENT INVESTIGATIONS WITH COLCHICINE AND PHYSOSTIGMINE
BROSSI, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) : 2311 - 2319
[2] OXIDATION BY SILVER CARBONATE ON CELITE .13. PREPARATION OF LACTONES
FETIZON, M
GOLFIER, M
LOUIS, JM
[J]. TETRAHEDRON, 1975, 31 (02) : 171 - 176
[3] ASYMMETRIC ALKYLATION OF OXINDOLES - AN APPROACH TO THE TOTAL SYNTHESIS OF (-)-PHYSOSTIGMINE
LEE, TBK
WONG, GSK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) : 872 - 875
[4] A CHIRAL TOTAL SYNTHESIS OF (-)-PHYSOSTIGMINE
NODE, M
HAO, X
FUJI, K
[J]. CHEMISTRY LETTERS, 1991, (01) : 57 - 60
[5] ALKALOIDS OF PHYSOSTIGMA VENENOSUM .PART I. STRUCTURE OF PHYSOVENINE
ROBINSON, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1964, (APR): : 1503 - &
[6] TOTAL SYNTHESES OF (+/-)-PHYSOVENINE AND (+/-)-PHYSOSTIGMINE - AN APPLICATION OF TANDEM ELECTROCYCLIC-[3,3]SIGMATROPIC REACTION OF BENZOCYCLOBUTENES
SHISHIDO, K
SHITARA, E
KOMATSU, H
HIROYA, K
FUKUMOTO, K
KAMETANI, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) : 3007 - 3011
[7] EXPEDIENT PREPARATION AND ENANTIOMERIZATION OF OPTICALLY PURE DICYCLOPENTADIENONE (TRICYCLO[5.2.1.0(2,6)]DECA-4,8-DIEN-3-ONE)
TAKANO, S
INOMATA, K
TAKAHASHI, M
OGASAWARA, K
[J]. SYNLETT, 1991, (09) : 636 - 638
[8] THE ENANTIOCONTROLLED TOTAL SYNTHESIS OF NATURAL (-)-GONIOMITINE
TAKANO, S
SATO, T
INOMATA, K
OGASAWARA, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (07) : 462 - 464
[9] ENANTIOCONVERGENT ROUTE TO ALPHA-CUPARENONE FROM DICYCLOPENTADIENE
TAKANO, S
INOMATA, K
OGASAWARA, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (05) : 271 - 272
[10] TAKANO S, 1982, CHEM PHARM BULL, V30, P2641

← 1 2 →