SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .1. SYNTHESIS OF ENANTIOMERIC PAIRS OF THE ABE RING-SYSTEMS OF QUINOCARCIN

被引：18

作者：

SAITO, S ^{[1
]}

TAMURA, O ^{[1
]}

KOBAYASHI, Y ^{[1
]}

MATSUDA, F ^{[1
]}

KATOH, T ^{[1
]}

TERASHIMA, S ^{[1
]}

机构：

[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 21期

关键词：

ASYMMETRIC SYNTHESIS; QUINOCARCIN; ANTITUMOR ANTIBIOTIC; ABE RING SYSTEM; DIASTEREOSELECTIVE REDUCTION; 4-O-BENZYL-2,3-O-ISOPROPYLIDENETHREOSE;

D O I：

10.1016/S0040-4020(01)80641-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomeric pairs of the ABE ring system (5 and ent-5) and its analogues (6, ent-6, 7, and ent-7) of quinocarcin (1), a prominent antitumor antibiotic, were synthesized in >95% ee with an aim to elucidate structure-activity relationships of 1. The key step of the synthesis includes novel diastereoselective reduction of 3,4-dihydroisoquinoline derivatives 25 and ent-25, wherein each enantiomer of 4-O-benzyl-2,3-O-isopropylidene-threose (I and ent-I) is employed as a chiral auxiliary.

引用

页码：6193 / 6208

页数：16

共 50 条

[31] SYNTHETIC AND BIOLOGICAL STUDIES OF COMPACTIN AND RELATED-COMPOUNDS .3. SYNTHESIS OF THE HEXALIN PORTION OF COMPACTIN
ROSEN, T
TASCHNER, MJ
THOMAS, JA
HEATHCOCK, CH
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08): : 1190 - 1201
[32] SYNTHETIC STUDIES ON CYCLITOLS AND RELATED-COMPOUNDS .4. FACILE SYNTHESIS OF AMINOCYCLITOLS FROM CYCLOHEXENE
KISO, M
KOBAYASHI, T
HASEGAWA, A
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1980, 44 (01): : 169 - 173
[33] SYNTHETIC AND BIOLOGICAL STUDIES OF COMPACTIN AND RELATED-COMPOUNDS .2. SYNTHESIS OF THE LACTONE MOIETY OF COMPACTIN
ROSEN, T
TASCHNER, MJ
HEATHCOCK, CH
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21): : 3994 - 4003
[34] SYNTHESIS PSEUDO-OLIGOSACCHARIDIC GLYCOSIDASE INHIBITORS .1. SYNTHESIS OF ADIPOSIN-1 AND RELATED-COMPOUNDS
OGAWA, S
IWASAWA, Y
TOYOKUNI, T
SUAMI, T
CARBOHYDRATE RESEARCH, 1985, 141 (01) : 29 - 40
[35] SYNTHETIC STUDIES OF RISHITIN AND RELATED-COMPOUNDS .9. PI-CYCLIZATION - THE SYNTHESIS OF (+/-)-SOLAVETIVONE AND (+/-)-HINESOL
MURAI, A
SATO, S
MASAMUNE, T
TETRAHEDRON LETTERS, 1981, 22 (11) : 1033 - 1036
[36] SYNTHETIC COMPOUNDS RELATED TO CARDENOLIDES .1. SYNTHESIS OF LACTONE DEOXYBENZOIN GLUCOSIDES
PRIGENT, AF
CIER, A
GROUILLER, A
PACHECO, H
CHIMICA E L INDUSTRIA-MILAN, 1972, 7 (04): : 307 - +
[37] STUDIES ON THE PHYTOALEXINS .36. A GENERAL SYNTHETIC APPROACH OF SPIROVETIVANES - THE SYNTHESIS OF (+/-)-SOLAVETIVONE, (+/-)-HINESOL, AND RELATED-COMPOUNDS
MURAI, A
SATO, S
MASAMUNE, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (08) : 2276 - 2281
[38] STUDIES ON PYRROLIZIDINES AND RELATED-COMPOUNDS .5. SYNTHESIS OF DELTA-1[9] AND OR DELTA-8[9]-DEHYDROINDOLIZIDINES AND RELATED-COMPOUNDS
MIYANO, S
FUJII, S
YAMASHITA, O
TORAISHI, N
SUMOTO, K
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (06) : 1465 - 1468
[39] STUDIES ON THE IRIDOID RELATED-COMPOUNDS .1. ON THE ANTIMICROBIAL ACTIVITY OF AUCUBIGENIN AND CERTAIN IRIDOID AGLYCONES
ISHIGURO, K
YAMAKI, M
TAKAGI, S
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1982, 102 (08): : 755 - 759
[40] SYNTHETIC STUDIES IN CARBOCYCLIC SYSTEMS .1. A NEW SYNTHESIS OF NOPINONE
MURTHI, GSS
MAZUMDER, A
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1981, 20 (04): : 339 - 340

← 1 2 3 4 5 →