Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-lodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal DeCanolides and Derivatives

被引：5

作者：

Sherwood, Alexander M. ^{[1
]}

Williamson, Samuel E. ^{[1
]}

Johnson, Stephanie N. ^{[1
]}

Yilmaz, Anil ^{[1
]}

Day, Victor W. ^{[1
]}

Prisinzano, Thomas E. ^{[1
]}

机构：

[1] Univ Kansas, Sch Pharm, Dept Med Chem, Lawrence, KS 66047 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 02期

基金：

美国国家科学基金会;

关键词：

RING-CLOSING METATHESIS; HOMOPROPARGYLIC ALCOHOLS; HOMOALLYL ALCOHOLS; MEDIATED REACTIONS; NATURAL-PRODUCTS; MACROCYCLIZATION; LACTONES; REAGENT; KETONE;

D O I：

10.1021/acs.joc.7b02324

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.

引用

页码：980 / 992

页数：13

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