Application of the intramolecular vinylogous Morita-Baylis-Hillman reaction toward the synthesis of the spinosyn A tricyclic nucleus

被引：75

作者：

Mergott, DJ ^{[1
]}

Frank, SA ^{[1
]}

Roush, WR ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 18期

关键词：

D O I：

10.1021/ol026540d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A concise synthesis of the spinosyn A tricyclic nucleus 27 has been developed by a route featuring a one-pot tandem intramolecular Diels-Alder reaction and intramolecular vinylogous Morita-Baylis-Hillman cyclization in which five stereocenters in tricycle 10 are set with excellent selectivity.

引用

收藏

页码：3157 / 3160

页数：4

相关论文

共 27 条

[1] TRIS(TRIMETHYLSILYL)SILANE AS A RADICAL-BASED REDUCING AGENT IN SYNTHESIS [J].

BALLESTRI, M ;

CHATGILIALOGLU, C ;

CLARK, KB ;

GRILLER, D ;

GIESE, B ;

KOPPING, B .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :678-683

[2] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[3] STEREOCONTROL IN THE INTRAMOLECULAR DIELS-ALDER REACTION .7. USE OF THE TRIMETHYLSILYL GROUP AS A REMOVABLE STEREOCONTROL ELEMENT TO PROVIDE GREATLY ENHANCED LEVELS OF DIASTEREOSELECTION [J].

BOECKMAN, RK ;

BARTA, TE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (18) :3421-3423

[4] ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS [J].

CHATGILIALOGLU, C .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) :188-194

[5]

Crouse GD, 2001, PEST MANAG SCI, V57, P177, DOI 10.1002/1526-4998(200102)57:2<177::AID-PS281>3.0.CO

[6]

2-Z

[7]

Dagani R, 1999, CHEM ENG NEWS, V77, P5

[8] 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

[9] TOTAL SYNTHESIS OF (+)-A83543A [(+)-LEPICIDIN-A] [J].

EVANS, DA ;

BLACK, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4497-4513

[10] Studies on the synthesis of (-)-spinosyn A: Application of the steric directing group strategy to transannular Diels-Alder reactions [J].

Frank, SA ;

Roush, WR .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4316-4324