C-19 QUASSINOIDS - TOTAL SYNTHESIS OF DL-SAMADERIN-B

被引：23

作者：

GRIECO, PA

PINEIRONUNEZ, MM

机构：

[1] Ernest E. Campaigne and Marvin Carmack Laboratory of Organic Chemistry, Department of Chemistry, Indiana University, Bloomington

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 17期

关键词：

D O I：

10.1021/ja00096a018

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of the novel C-19 quassinoid dl-samaderin B (2) is described. The synthesis commences with the known racemic pentacyclic ketone 6, which permits introduction of the C(11), C(12) trans diaxial arrangement of the hydroxyl groups in ring C. The synthesis features a copper(II)-mediated ring contraction of a delta-lactone (28) to a gamma-lactone (29). Subsequent elaboration of the ring A 1 beta-hydroxy-2-oxo-Delta(3,4) olefin unit, cleavage of the C(7), C(11) methoxymethyl ethers, selective oxidation at C(7), and deprotection of the C(1) hydroxyl affords samaderin B (2).

引用

页码：7606 / 7615

页数：10

共 25 条

[1] GENERAL-SYNTHESIS OF PENTACYCLIC QUASSINOIDS [J].

BATT, DG ;

TAKAMURA, N ;

GANEM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (11) :3353-3354

[2]

BYLBER J, 1962, B SOC CHIM FR, P1715

[3] SYNTHESIS OF 15-DEOXY-16-BETA-ETHOXYBRUCEANTIN AND SYNTHETIC EFFORTS TOWARD BRUCEANTIN [J].

CHIU, CKF ;

GOVINDAN, SV ;

FUCHS, PL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :311-323

[4] SYNTHESIS OF A MODEL FOR THE BCE RING-SYSTEM OF BRUCEANTIN - CAVEAT ON THE CYCLOHEXENE -] TRANS DIAXIAL DIOL CONVERSION [J].

DAILEY, OD ;

FUCHS, PL .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (02) :216-236

[5] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[6] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[7] SYNTHETIC STUDIES ON QUASSINOIDS - TOTAL SYNTHESIS OF (-)-CHAPARRINONE, (-)-GLAUCARUBOLONE, AND (+)-GLAUCARUBINONE [J].

GRIECO, PA ;

COLLINS, JL ;

MOHER, ED ;

FLECK, TJ ;

GROSS, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6078-6093

[8] DRAMATIC RATE ACCELERATIONS OF DIELS-ALDER REACTIONS IN 5-M LITHIUM PERCHLORATE DIETHYL-ETHER - THE CANTHARIDIN PROBLEM REEXAMINED [J].

GRIECO, PA ;

NUNES, JJ ;

GAUL, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4595-4596

[9]

GRIECO PA, 1993, J AM CHEM SOC, V115, P5841

[10]

Hassall C. H., 1957, ORG REACTIONS, V9, P73

← 1 2 3 →