Total synthesis of (+)-tanikolide via oxidative lactonization

被引:32
作者
Schomaker, JM [1 ]
Borhan, B [1 ]
机构
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
关键词
D O I
10.1039/b311432e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+)-Tanikolide has been synthesized in eight linear steps with a 31% overall yield. The key step in the synthesis utilizes a recently developed tandem oxidative cleavage-lactonization of a precursor alkenol to deliver the lactone moiety.
引用
收藏
页码:621 / 624
页数:4
相关论文
共 24 条
[21]   Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: An organometallic ozonolysis [J].
Travis, BR ;
Narayan, RS ;
Borhan, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) :3824-3825
[22]   Optically active allenes from β-lactone templates:: Asymmetric total synthesis of (-)-malyngolide [J].
Wan, ZH ;
Nelson, SG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (42) :10470-10471
[23]   A new synthesis of tanikolide [J].
Zhai, HB ;
Chen, QS ;
Zhao, JR ;
Luo, SJ ;
Jia, XS .
TETRAHEDRON LETTERS, 2003, 44 (14) :2893-2894
[24]   Total synthesis of (±)tanikolide [J].
Zhang, RZ ;
Wang, ZQ ;
Wei, FP ;
Huang, YR .
SYNTHETIC COMMUNICATIONS, 2002, 32 (14) :2187-2194