Total Synthesis of (+)-Iresin

被引：14
作者：
Wang, Bian-Lin [1 ]
Gao, Hai-Tao [1 ]
Li, Wei-Dong Z. [1 ,2 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Chongqing Univ, Innovat Drug Res Ctr, Chongqing 401331, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 10期
关键词：
EPOXY ESTER-ORTHOESTER; DRIMANE SESQUITERPENOIDS; ABSOLUTE CONFIGURATION; BIOLOGICAL-ACTIVITY; SILVER CARBONATE; INNER SALT; IRESIN; TERPENOIDS; OXIDATION; REARRANGEMENT;
D O I：
10.1021/acs.joc.5b00365
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first asymmetric total synthesis of (+)-iresin (4), an historically important ent-Drimane sesquiterpene lactone, was realized from aldehyde 3 via cyclic orthoester 6 in 5 steps. Notable transformations in this synthesis include a tandem trifluoroperacetic acid (TEPAA)-mediated Baeyer-Villiger oxidation-olefin epoxidation-epoxy ester cyclization, regioselective Burgess dehydration, and regioselective Fetizon oxidative lactonization.
引用
收藏
页码：5296 / 5301
页数：6
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