Chiral aziridinyl radicals: An application to the synthesis of the core nucleus of FR-900482

被引：91

作者：

Ziegler, FE

Belema, M

机构：

[1] Sterling Chemistry Laboratory, Yale University, New Haven

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 04期

关键词：

D O I：

10.1021/jo961992n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric route to the core nucleus of the antitumor agent FR-900482 utilizes the cyclization of an aziridinyl radical into a functionalized indole nucleus. The route employs a selective Polonovski reaction and the Hootele-Dmitrienko rearrangement to install two oxygen atoms.

引用

收藏

页码：1083 / 1094

页数：12

相关论文

共 64 条

[41] CATALYTIC RING-CLOSING METATHESIS OF DIENES - APPLICATION TO THE SYNTHESIS OF 8-MEMBERED RINGS [J].

MILLER, SJ ;

KIM, SH ;

CHEN, ZR ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) :2108-2109

[42] SYNTHESIS OF 1,2-FUSED INDOLES BY RADICAL CYCLIZATION [J].

MOODY, CJ ;

NORTON, CL .

TETRAHEDRON LETTERS, 1995, 36 (49) :9051-9052

[43] AMINOBENZOIC ACID DIURETICS .7. 3-SUBSTITUTED 4-PHENYL-5-SULFAMOYLBENZOIC, 4-ARYLCARBONYL-5-SULFAMOYLBENZOIC, AND 4-ARYLMETHYL-5-SULFAMOYLBENZOIC ACIDS AND RELATED COMPOUNDS [J].

NIELSEN, OBT ;

BRUUN, H ;

BRETTING, C ;

FEIT, PW .

JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (01) :41-50

[44] A HIGH-YIELD CONVERSION OF TRANS-RH(CL)(CO)(PPH3)2 TO RH(CL)(PPH3)3 [J].

OCONNOR, JM ;

MA, JN .

INORGANIC CHEMISTRY, 1993, 32 (09) :1866-1867

[45] NOVEL TEMPLATE EFFECTS OF DISTANNOXANE CATALYSTS IN HIGHLY EFFICIENT TRANSESTERIFICATION AND ESTERIFICATION [J].

OTERA, J ;

DANOH, N ;

NOZAKI, H .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5307-5311

[46] TOTAL SYNTHESIS OF (+/-)-FR-900482 [J].

SCHKERYANTZ, JM ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) :4722-4723

[47] A NEW ANTITUMOR ANTIBIOTIC, FR-900482 .3. ANTITUMOR-ACTIVITY IN TRANSPLANTABLE EXPERIMENTAL-TUMORS [J].

SHIMOMURA, K ;

HIRAI, O ;

MIZOTA, T ;

MATSUMOTO, S ;

MORI, J ;

SHIBAYAMA, F ;

KIKUCHI, H .

JOURNAL OF ANTIBIOTICS, 1987, 40 (05) :600-606

[48]

SHIMOMURA K, 1988, CANCER RES, V48, P1166

[49] RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION [J].

STILL, WC ;

KAHN, M ;

MITRA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2923-2925

[50] STEREOSELECTIVE TOTAL SYNTHESES OF (+1-)-YOHIMBINE,(+1-)-PSI-YOHIMBINE,AND (+1-)-BETA-YOHIMBINE [J].

STORK, G ;

GUTHIKON.RN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (14) :5109-&

← 1 2 3 4 5 6 7 →