SYNTHESIS AND PRELIMINARY EVALUATION OF THE FREDERICAMYCIN-A ABCDE RING-SYSTEM

被引：56

作者：

BOGER, DL ^{[1
]}

JACOBSON, IC ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT MED CHEM,W LAFAYETTE,IN 47907

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 06期

关键词：

D O I：

10.1021/jo00006a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise preparation of 2 constituting the fully functionalized fredericamycin A ABCDE ring system is detailed and is based on the implementation of a regiospecific, intermolecular alkyne-chromium carbene complex benzannulation reaction for introduction of the AB ring system and a facile aldol closure for introduction of the spirocyclic CD ring system. Chemical and preliminary biological comparisons of 2 with fredericamycin are described.

引用

页码：2115 / 2122

页数：8

共 64 条

[1] AIDHEN IS, 1989, TETRAHEDRON LETT, V30, P5323
[2] MODEL STUDIES AIMED AT THE SYNTHESIS OF FREDERICAMYCIN-A - A SIMPLE O-QUINODIMETHANE ROUTE TO THE SPIRO NAPHTHALENE PORTION
BACH, RD
KLIX, RC
[J]. TETRAHEDRON LETTERS, 1986, 27 (18) : 1983 - 1986
[3] A MERCURY-MEDIATED ACYL MIGRATION IN A PINACOL-TYPE REARRANGEMENT - MODEL STUDIES TOWARD THE SYNTHESIS OF FREDERICAMYCIN-A
BACH, RD
KLIX, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) : 749 - 752
[4] CONCERTED 1,2-CARBONYL MIGRATIONS IN ORGANIC-SYNTHESIS - A PRACTICAL SYNTHESIS OF SPIRO CYCLIC 1,3-DIKETONES
BACH, RD
KLIX, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) : 5438 - 5440
[5] SYNTHESIS OF SPIRO-COMPOUNDS RELATED TO FREDERICAMYCIN-A
BENNETT, SM
CLIVE, DLJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (11) : 878 - 880
[6] STREPTONIGRIN AND LAVENDAMYCIN PARTIAL STRUCTURES - PROBES FOR THE MINIMUM, POTENT PHARMACOPHORE OF STREPTONIGRIN, LAVENDAMYCIN, AND SYNTHETIC QUINOLINE-5,8-DIONES
BOGER, DL
YASUDA, M
MITSCHER, LA
DRAKE, SD
KITOS, PA
THOMPSON, SC
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) : 1918 - 1928
[7] STUDIES ON THE TOTAL SYNTHESIS OF FREDERICAMYCIN-A - DEVELOPMENT OF AN INTERMOLECULAR ALKYNE-CHROMIUM CARBENE COMPLEX CYCLIZATION APPROACH TO THE ABCDE RING-SYSTEM
BOGER, DL
JACOBSON, IC
[J]. TETRAHEDRON LETTERS, 1989, 30 (16) : 2037 - 2040
[8] STUDIES OF THE TOTAL SYNTHESIS OF FREDERICAMYCIN-A - PREPARATION OF KEY PARTIAL STRUCTURES AND DEVELOPMENT OF AN INTERMOLECULAR ALKYNE CHROMIUM CARBENE COMPLEX BENZANNULATION CYCLIZATION APPROACH TO THE ABCD(E) RING-SYSTEM
BOGER, DL
JACOBSON, IC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1919 - 1928
[9] BOS MA, UNPUB
[10] SYNTHESIS OF SPIROCYCLIC DIKETONES RELATED TO FREDERICAMYCIN-A
BRAUN, M
VEITH, R
[J]. TETRAHEDRON LETTERS, 1986, 27 (02) : 179 - 182

← 1 2 3 4 5 6 7 →