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

页码：5296 / 5301

页数：6

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