A new tandem route to angular tetraquinanes. Synthesis of the waihoensene ring system

被引：65

作者：

ErgUden, JK ^{[1
]}

Moore, HW ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 03期

关键词：

D O I：

10.1021/ol990023m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] This paper describes a new tandem reaction sequence leading to angularly fused polyquinanes from squaric acid-derived bicyclo[6.3.0]-undecadienediones. Such compounds undergo a dual Michael addition, The enolate form in the first intermolecular addition undergoes the second intramolecuar transannular addition to give the angular polyquinanes, A particularly interesting example is a catalytic transformation of cis-13-3-methylyricyclo[10.3.0.0(4,9)]pentadeca-4(5),12(13)-diene-3,14-diene to (3R*,3aS*,5aR*,9a*,11aR*)S-methyl-l,2,3,5,5a,6,7,1 O,ll,lla-decahydro4Hpentaleno[Ga,l-c]indene-2,10-dione, a compound having the tetracydic ring system found in the natural product waihoensene, The mechanism and synthetic scope of these reactions are discussed.

引用

页码：375 / 377

页数：3

共 11 条

[1] Waihoensene. A new Laurenene-related diterpene from Podocarpus totara var waihoensis [J].