STEREOSELECTIVE TOTAL SYNTHESIS OF RACEMIC STACHENONE

被引:16
作者
MONTI, SA
YANG, YL
机构
[1] Department of Chemistry, The University of Texas at Austin, Austin
关键词
D O I
10.1021/jo01319a067
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The C/D ring synthon bicyclo[3.2.1]octenedione (4), available from acid-catalyzed rearrangement of the bicyclo[2.2.2]octenol (7), was converted into the trans-fused B-C/D tricyclic derivative 5 by aldol cyclization and dissolving metal reduction and then into trans-anti-trans tetracyclic diterpene stachenone (1) by Robinson ring annelation and reductive alkylation in an overall yield of 16% from the starting bicyclo[2.2.2]octenone (3). © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:897 / 898
页数:2
相关论文
共 19 条
[1]   STRUCTURE OF SOME DITERPENES FROM TAMBOOTI WOOD, SPIROSTACHYS AFRICANA SOND [J].
BAARSCHERS, WH ;
JOHNSON, LRF ;
HORN, DHS .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (10) :4046-&
[2]   REGIOSPECIFICITY IN ENOLATE REACTIONS WITH ALPHA-SILYL VINYL KETONES - APPLICATION TO STEROID TOTAL SYNTHESIS [J].
BOECKMAN, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (19) :6179-6181
[3]  
EVANS DA, 1972, TETRAHEDRON LETT, P121
[4]   RESIN ACIDS .9. CATIONIC CYCLIZATION OF PIMARIC ACID DERIVATIVES . PARTIAL SYNTHEIS OF (-)-HIBAENE [J].
HERZ, W ;
PINDER, AK ;
MIRRINGT.RN .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) :2257-&
[5]  
HOUSE HO, 1972, MODERN SYNTHETIC REA, P174
[6]  
IRELAND RE, 1965, TETRAHEDRON LETT, P2627
[7]   NOVEL STEREOSPECIFIC SYNTHESIS OF A POTENTIAL INTERMEDIATE FOR PREPARATION OF TETRACYCLIC DITERPENES FROM DIHYDROBENZOCYCLOBUTENE DERIVATIVES [J].
KAMETANI, T ;
NEMOTO, H ;
FUKUMOTO, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (11) :400-401
[8]  
MAHN DDK, 1975, TETRAHEDRON, V31, P1897
[9]   TOTAL SYNTHESIS OF (+/-)-HINESOL [J].
MARSHALL, JA ;
BRADY, SF .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (12) :4068-&
[10]   REARRANGEMENT APPROACHES TO POLYCYCLIC SKELETONS .1. BRIDGEHEAD-SUBSTITUTED BICYCLO[3.2.1]OCTENE DERIVATIVES FROM BICYCLO[2.2.2]OCTENE PRECURSORS [J].
MONTI, SA ;
CHEN, SC ;
YANG, YL ;
YUAN, SS ;
BOURGEOIS, OP .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4062-4069