STUDIES TOWARD THE TOTAL SYNTHESIS OF (+)-PTILOMYCALIN-A - USE OF A TETHERED BIGINELLI CONDENSATION FOR THE PREPARATION OF AN ADVANCED TRICYCLIC INTERMEDIATE

被引：51

作者：

OVERMAN, LE

RABINOWITZ, MH

机构：

[1] Department of Chemistry, University of California, Irvine

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 12期

关键词：

D O I：

10.1021/jo00064a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An intramolecular ureidoaldehyde condensation, 16 + (R)-14 --> 19, is the key step in a seven-step preparation of the enantiopure spirotricycle 23, a potential intermediate for the enantioselective total synthesis of ptilomycalin A.

引用

页码：3235 / 3237

页数：3

共 20 条

[1] SUBSTITUTED 1,4-DIHYDROPYRIMIDINES .3. SYNTHESIS OF SELECTIVELY FUNCTIONALIZED 2-HETERO-1,4-DIHYDROPYRIMIDINES [J].

ATWAL, KS ;

ROVNYAK, GC ;

OREILLY, BC ;

SCHWARTZ, J .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5898-5907

[2]

Biginilli P., 1893, GAZZ CHIM ITAL, V23, P360

[3]

BROWN DJ, 1962, PYRIMIDINES, P440

[4]

BROWN DJ, 1982, COMPREHENSIVE HETERO, V3, P117

[5] PHOTOCHEMISTRY OF SOME CARBONYL-CONJUGATED 1,5-HEXADIENES [J].

CRANDALL, JK ;

MAYER, CF .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (09) :3049-&

[6]

DESLONGCHAMPS P, 1983, STEREOELECTRONIC EFF, pCH1

[7] Researches on pyrimidines CXXX Synthesis of 2-keto-1,2,3,4-tetrahydropyrimidines [J].

Folkers, K ;

Harwood, HJ ;

Johnson, TB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1932, 54 :3751-3758

[8]

HARBOUR GC, 1981, J AM CHEM SOC, V103, P5606

[9] ALKYLATION OF DIANIONS OF BETA-KETO-ESTERS [J].

HUCKIN, SN ;

WEILER, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1082-1087

[10] CRAMBESCIDINS - NEW ANTIVIRAL AND CYTOTOXIC COMPOUNDS FROM THE SPONGE CRAMBE-CRAMBE [J].

JARESERIJMAN, EA ;

SAKAI, R ;

RINEHART, KL .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5712-5715

← 1 2 →