TOTAL SYNTHESIS OF (+/-)-ILLUDIN-M

被引：76

作者：

KINDER, FR

BAIR, KW

机构：

[1] Oncology Research Program, Preclinical Research, Sandoz Research Institute, Sandoz Pharmaceuticals Corporation, New Jersey 07936-1080, 59 Route 10, East Hanover

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 23期

关键词：

D O I：

10.1021/jo00102a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-Illudin M (1) was synthesized in six steps starting from 1-acetyl-1-(diazoacetyl)cyclopropane (4) and 4-bromo-5,5-dimethyl-2-cyclopentenone (5). The key step of the synthesis featured a carbonyl ylide 1,3-dipolar cycloaddition reaction that was mediated by the formation of a rhodium(II) carbenoid from 4 and catalytic rhodium(II) diacetate.

引用

页码：6965 / 6967

页数：3

共 15 条

[1] ANTIBIOTIC SUBSTANCES FROM BASIDIOMYCETES .7. CLITOCYBE ILLUDENS
ANCHEL, M
HERVEY, A
ROBBINS, WJ
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1950, 36 (05) : 300 - 305
[2] PRECLINICAL EVALUATION OF ILLUDINS AS ANTICANCER AGENTS - BASIS FOR SELECTIVE CYTOTOXICITY
KELNER, MJ
MCMORRIS, TC
TAETLE, R
[J]. JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1990, 82 (19): : 1562 - 1565
[3] MATSUMOT.T, 1970, TETRAHEDRON LETT, P1171
[4] SYNTHESIS OF 5,5-DIMETHYL-4-ACETOXY-2-CYCLOPENTENONE AND 5-METHYL TERT 5-ACETOXYMETHYL-R-4-ACETOXY-2-CYCLOPENTENONE INTERMEDIATES FOR ILLUDIN M AND S
MATSUMOTO, T
MATSUMOT.S
KAGAWA, S
ICHIHARA, A
SHIN, H
SHIRAHAM.H
SAITO, K
SAKAN, F
HASHIMOT.H
NISHIDA, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (04) : 1140 - +
[5] STRUCTURE OF LAMPTEROL (ILLUDIN S)
MATSUMOTO, T
SHIRAHAMA, H
ICHIHARA, A
FUKUOKA, Y
TAKAHASHI, Y
MORI, Y
WATANABE, M
[J]. TETRAHEDRON, 1965, 21 (09) : 2671 - +
[6] TOTAL SYNTHESIS OF DL-ILLUDIN M
MATSUMOTO, T
SHIRAHAMA, H
ICHIHARA, A
SHIN, H
KAGAWA, S
SAKAN, F
MATSUMOTO, S
NISHIDA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (12) : 3280 - +
[7] STRUCTURES OF BASIDIOMYCETE METABOLITES ILLUDIN S AND ILLUDIN M
MCMORRIS, TC
ANCHEL, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (06) : 831 - &
[8] STRUCTURE-ACTIVITY-RELATIONSHIPS OF ILLUDINS - ANALOGS WITH IMPROVED THERAPEUTIC INDEX
MCMORRIS, TC
KELNER, MJ
WANG, W
ESTES, LA
MONTOYA, MA
TAETLE, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) : 6876 - 6883
[9] STRUCTURE AND REACTIVITY OF ILLUDINS
MCMORRIS, TC
KELNER, MJ
CHADHA, RK
SIEGEL, JS
MOON, SS
MOYA, MM
[J]. TETRAHEDRON, 1989, 45 (17) : 5433 - 5440
[10] MCMORRIS TC, 1987, CANCER RES, V47, P3186

← 1 2 →