2 DIVERSE MODES OF AROMATIZATION OF A NEW 10-MEMBERED RING ANALOG OF NEOCARZINOSTATIN CHROMOPHORE

被引：63

作者：

FUJIWARA, K ^{[1
]}

KURISAKI, A ^{[1
]}

HIRAMA, M ^{[1
]}

机构：

[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(00)97613-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thiol addition to 6,6-dimethylbicyclo[8.3.0]trideca-9,13-diene-2,7-diyn-4-one (2), a new ketone analogue of neocarzinostatin chromophore, caused the anticipated aromatization under anaerobic conditions, while the reaction under the aerobic conditions culminated in the unexpected formation of skeletally distinct products. © 1990.

引用

页码：4329 / 4332

页数：4

共 17 条

[1] THE STRUCTURE OF NEOCARZINOSTATIN CHROMOPHORE POSSESSING A NOVEL BICYCLO-[7,3,0]DODECADIYNE SYSTEM
EDO, K
MIZUGAKI, M
KOIDE, Y
SETO, H
FURIHATA, K
OTAKE, N
ISHIDA, N
[J]. TETRAHEDRON LETTERS, 1985, 26 (03) : 331 - 334
[2] KINETICS OF THIOL-DISULFIDE EXCHANGE .2. OXYGEN-PROMOTED FREE-RADICAL EXCHANGE BETWEEN AROMATIC THIOLS AND DISULFIDES
FAVA, A
REICHENBACH, G
PERON, U
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (25) : 6696 - +
[3] MECHANISM OF ACTIVATION OF THE ANTITUMOR ANTIBIOTIC NEOCARZINOSTATIN BY MERCAPTAN AND SODIUM-BOROHYDRIDE
HENSENS, OD
GOLDBERG, IH
[J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (05) : 761 - 768
[4] THE 10-MEMBERED RING ANALOGS OF NEOCARZINOSTATIN CHROMOPHORE - DESIGN, SYNTHESIS, AND MODE OF DECOMPOSITION
HIRAMA, M
FUJIWARA, K
SHIGEMATU, K
FUKAZAWA, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) : 4120 - 4122
[5] ISHIDA N, 1965, J ANTIBIOT, V18, P68
[6] ACTIVATION OF NEOCARZINOSTATIN CHROMOPHORE AND FORMATION OF NASCENT DNA DAMAGE DO NOT REQUIRE MOLECULAR-OXYGEN
KAPPEN, LS
GOLDBERG, IH
[J]. NUCLEIC ACIDS RESEARCH, 1985, 13 (05) : 1637 - 1648
[7] SEQUENCE-SPECIFIC, STRAND-SELECTIVE, AND DIRECTIONAL BINDING OF NEOCARZINOSTATIN CHROMOPHORE TO OLIGODEOXYRIBONUCLEOTIDES
LEE, SH
GOLDBERG, IH
[J]. BIOCHEMISTRY, 1989, 28 (03) : 1019 - 1026
[8] ESPERAMICINS, A CLASS OF POTENT ANTITUMOR ANTIBIOTICS - MECHANISM OF ACTION .4.
LONG, BH
GOLIK, J
FORENZA, S
WARD, B
REHFUSS, R
DABROWIAK, JC
CATINO, JJ
MUSIAL, ST
BROOKSHIRE, KW
DOYLE, TW
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (01) : 2 - 6
[9] STUDIES ON THE SYNTHESIS OF THE ANTITUMOR AGENTS ESPERAMICIN-A1 CALICHEAMICIN-GAMMA-1 - STEREOSPECIFIC SYNTHESIS OF THE 12-BETA-HYDROXYBICYCLO[7.3.1]DIYNENE CORE STRUCTURE VIA A CO2(CO)6-ACETYLENE-MEDIATED SYNCLINAL ALDOL REACTION
MAGNUS, P
ANNOURA, H
HARLING, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1709 - 1711
[10] PROPOSED STRUCTURE OF THE NEOCARZINOSTATIN CHROMOPHORE-METHYL THIOGLYCOLATE ADDUCT - A MECHANISM FOR THE NUCLEOPHILIC ACTIVATION OF NEOCARZINOSTATIN
MYERS, AG
[J]. TETRAHEDRON LETTERS, 1987, 28 (39) : 4493 - 4496

← 1 2 →