Synthesis of C14-Desmethylene Corialactone D and Discovery of Inhibitors of Nerve Growth Factor Mediated Neurite Outgrowth

被引：15

作者：

Leon, Robert M. ^{[1
]}

Ravi, Divya ^{[2
]}

An, Jennifer S. ^{[2
]}

del Genio, Carmen L. ^{[2
]}

Rheingold, Arnold L. ^{[3
]}

Gaur, Arti B. ^{[2
]}

Micalizio, Glenn C. ^{[1
]}

机构：

[1] Dartmouth Coll, Dept Chem, Burke Lab, Hanover, NH 03755 USA

[2] Dartmouth Coll, Geisel Sch Med, 1 Med Ctr Dr, Lebanon, NH 03756 USA

[3] Univ Calif San Diego, Dept Chem, La Jolla, CA 92093 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 09期

基金：

美国国家卫生研究院;

关键词：

STEREOCONTROLLED TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; ENYNE CYCLOISOMERIZATION REACTION; PICROTOXANE SESQUITERPENES; ALKALOID SYNTHESIS; (-)-DENDROBINE; CORIANIN; (-)-PICROTOXININ; DEOXYGENATION;

D O I：

10.1021/acs.orglett.9b00921

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of C14-desmethylene corialactone D is described on the basis of strategic application of a metallacycle-mediated annulative cross-coupling reaction, a Still [2,3]-Wittig rearrangement, and Morken's hydroxyl-directed diboration reaction. While representing a convenient approach to access novel compositions of matter inspired by the sesquiterpenoid natural product class (including classic natural product synthesis targets including the picrotaxanes and dendrobine), these studies have led to the discovery of natural product-inspired agents that inhibit nerve growth factor (NGF)-mediated neurite outgrowth in PC-12 cells.

引用

页码：3193 / 3197

页数：5

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