Studies on C20-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton

被引：30

作者：

Hamlin, Amy M. ^{[1
]}

Lapointe, David ^{[1
]}

Owens, Kyle ^{[1
]}

Sarpong, Richmond ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 15期

基金：

美国国家卫生研究院;

关键词：

CHIRAL DIPHOSPHINE LIGAND; ALPHA-CYANO CARBOXYLATES; DITERPENOID ALKALOIDS; ACONITE ALKALOIDS; CYCLOISOMERIZATION APPROACH; CHEMICAL CONVERSION; SECONDARY-AMINES; MULTIPLE BONDS; K+ CHANNEL; OXIDATION;

D O I：

10.1021/jo501214b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The full details of a synthesis of the hetidine framework of the C-20-diterpenoid alkaloids and its conversion to the atisine core structure are reported. The application of the hetidine framework to the synthesis of dihydronavirine, which is the formal reduction product of the natural product navirine, is also described. Key to the success of these studies is the use of a Ga(III)-catalyzed cycloisomerization reaction of alkynylin denes to prepare a [6-7-6] framework that was advanced to the hetidine skeleton. Furthermore, a Michael/aldol sequence was developed for the construction of the bicyclo[2.2.2] framework that is characteristic of the hetidines and atisines.

引用

页码：6783 / 6800

页数：18

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