TOTAL SYNTHESIS OF (+)-LYCORICIDINE AND ITS 2-EPIMER FROM D-GLUCOSE

被引：81

作者：

CHIDA, N ^{[1
]}

OHTSUKA, M ^{[1
]}

OGAWA, S ^{[1
]}

机构：

[1] KEIO UNIV, FAC SCI & TECHNOL,DEPT APPL CHEM,3-14-1 HIYOSHI, KOHOKU KU, YOKOHAMA, KANAGAWA 223, JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 16期

关键词：

D O I：

10.1021/jo00068a045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective total synthesis of antimitotic alkaloid (+)-lycoricidine (1) and its 2-epimer (30) was accomplished starting from D-glucose. The key steps in this synthesis are (i) a catalytic version of the Ferrier rearrangement for the preparation of the optically active substituted cyclohexenone (the C-ring of lycoricidine) and (ii) a Pd-catalyzed intramolecular Heck-typE, reaction for construction of the phenanthridone skeleton. A preliminary biological assay revealed that the stereochemistry at the 2-position of lycoricidine plays an important role in its cytotoxic activity.

引用

页码：4441 / 4447

页数：7

共 72 条

[1] INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS
ABELMAN, MM
OH, T
OVERMAN, LE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) : 4130 - 4133
[2] NARCICLASINE-4-O-BETA-D-GLUCOPYRANOSIDE, A GLUCOSYLOXY AMIDIC PHENANTHRIDONE DERIVATIVE FROM PANCRATIUM-MARITIMUM
ABOUDONIA, AH
DEGIULIO, A
EVIDENTE, A
GABER, M
HABIB, AA
LANZETTA, R
ELDIN, AAS
[J]. PHYTOCHEMISTRY, 1991, 30 (10) : 3445 - 3448
[3] BARTON DHR, 1990, TETRAHEDRON, V46, P215
[4] SYNTHETIC METHODS FOR THE PREPARATION OF D-PSEUDO-SUGARS AND L-PSEUDO-SUGARS FROM D-GLUCOSE
BARTON, DHR
GERO, SD
CLEOPHAX, J
MACHADO, AS
QUICLETSIRE, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (17) : 1184 - 1186
[5] FUNCTIONALIZED CARBOCYCLES FROM CARBOHYDRATES .8. UNSATURATED CARBOHYDRATES .28. OBSERVATIONS ON THE CONVERSION OF 6-DEOXYHEX-5-ENOPYRANOSYL COMPOUNDS INTO 2-DEOXYINOSOSE DERIVATIVES
BLATTNER, R
FERRIER, RJ
HAINES, SR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2413 - 2416
[6] CRYSTALLINE PSEUDO-ALPHA-D-GLUCOPYRANOSE
BLATTNER, R
FERRIER, RJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (13) : 1008 - 1009
[7] NARCICLASINE - AN ANTIMITOTIC SUBSTANCE FROM NARCISSUS BULBS
CERIOTTI, G
[J]. NATURE, 1967, 213 (5076) : 595 - &
[8] STEREOSELECTIVE TOTAL SYNTHESIS OF (+)-LYCORICIDINE
CHIDA, N
OHTSUKA, M
OGAWA, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (35) : 4525 - 4528
[9] TOTAL SYNTHESIS OF ANTIBIOTIC HYGROMYCIN-A
CHIDA, N
OHTSUKA, M
NAKAZAWA, K
OGAWA, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) : 2976 - 2983
[10] SYNTHESIS OF OPTICALLY-ACTIVE SUBSTITUTED CYCLOHEXENONES FROM CARBOHYDRATES BY CATALYTIC FERRIER REARRANGEMENT
CHIDA, N
OHTSUKA, M
OGURA, K
OGAWA, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (07) : 2118 - 2121

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