Total Synthesis of (±)-Cafestol: A Late-Stage Construction of the Furan Ring Inspired by a Biosynthesis Strategy

被引：49

作者：

Zhu, Lili ^{[1
]}

Luo, Jisheng ^{[1
]}

Hong, Ran ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, CAS Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 08期

基金：

中国国家自然科学基金;

关键词：

METAL PEROXIDE REACTIONS; CATALYZED ENE REACTIONS; ENANTIOSELECTIVE POLYENE CYCLIZATION; ABSOLUTE CONFIGURATION; KAURANE DITERPENOIDS; EUDESMANE TERPENES; ORGANIC-SYNTHESIS; CAFESTOL; ACID; KAHWEOL;

D O I：

10.1021/ol500623w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient bioinspired approach to the total synthesis of (+/-)-cafestol features a late-stage installation of the furan ring with a mild Au-catalyzed cycloisomerization. The Et2AlCl-promoted aldehyde-ene cyclization and subsequent Friedel Crafts reaction deliver a requisite tricyclic system in gram scale with high stereo- and regioselectivity. Moreover, a highly stereoselective SmI(2)mediated aldehyde alkene radical cyclization furnishes the key bicyclo[3.2.1]octane skeleton to offer an advanced intermediate for the synthesis of other oxygenated ent-kaurene diterpenoids.

引用

页码：2162 / 2165

页数：4

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