SYNTHESIS OF 2 NOVEL SPIRO LACTONES RELATED TO THE B/C RING-SYSTEM OF BAKKENOLIDES BY RADICAL CYCLIZATION

被引：0

作者：

BACK, TG

GLADSTONE, PL

机构：

来源：

SYNLETT | 1993年 / 09期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of spiro lactones 2a and 2b was achieved by photochemically induced free-radical cyclization of allyl 1-(phenylseleno)-3-methyl-2-oxo-3-cyclopentenecarboxylate (4a) and its 4-methyl isomer (4b), respectively, followed by selenoxide elimination.

引用

收藏

页码：699 / 700

页数：2

相关论文

共 15 条

[1] ELECTROPHILIC CYCLIZATION OF AN OLEFINIC BETA-KETO ESTER [J].

ALDERDICE, M ;

WEILER, L .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (14) :2239-2241

[2] RADICAL-ADDITION OF VARIED FUNCTIONALITY VIA PHENYLSELENENYL TRANSFER [J].

BYERS, JH ;

HARPER, BC .

TETRAHEDRON LETTERS, 1992, 33 (46) :6953-6954

[3] DIRECT APPROACH TO THE BAKKANES - A SYNTHESIS OF (+/-)-HOMOGYNOLIDE-B [J].

COELHO, F ;

DEPRES, JP ;

BROCKSOM, TJ ;

GREENE, AE .

TETRAHEDRON LETTERS, 1989, 30 (05) :565-566

[4] ADDITIONS OF MALONONITRILE RADICALS TO ALKENES - NEW EXAMPLES OF 1,2-ASYMMETRIC INDUCTION IN IODINE AND PHENYLSELENIUM TRANSFER-REACTIONS [J].

CURRAN, DP ;

THOMA, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4436-4437

[5] APPLICATIONS OF [2,3]-SIGMATROPIC REARRANGEMENTS TO NATURAL-PRODUCTS SYNTHESIS - TOTAL SYNTHESIS OF (+/-)-BAKKENOLIDE-A (FUKINANOLIDE) [J].

EVANS, DA ;

SIMS, CL ;

ANDREWS, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (16) :5453-5461

[6]

FISCHER NH, 1979, PROGR CHEM ORGANIC N, P257

[7] AN APPROACH TO THE BAKKANES - A SHORT, STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-BAKKENOLIDE-A [J].

GREENE, AE ;

DEPRES, JP ;

COELHO, F ;

BROCKSOM, TJ .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3943-3945

[8]

GREENE AE, 1988, TETRAHEDRON LETT, V29, P5661

[9] STEREOSELECTIVE BAKKANE SYNTHESIS - (+/-)-PALMOSALIDE-C [J].

HARTMANN, B ;

DEPRES, JP ;

GREENE, AE ;

DELIMA, MEF .

TETRAHEDRON LETTERS, 1993, 34 (09) :1487-1490

[10] STEREOSELECTIVE SYNTHESIS OF HOMOGYNOLIDE-A, A BAKKANE FROM HOMOGYNE-ALPINA [J].

HARTMANN, B ;

KANAZAWA, AM ;

DEPRES, JP ;

GREENE, AE .

TETRAHEDRON LETTERS, 1991, 32 (06) :767-768