Synthetic Studies of Java']Javaberine A Based on Intramolecular Hydroamination of Alkenes

被引：0

作者：

Yamamoto, Yasutomo ^{[1
]}

Baba, Hiromi ^{[2
,3
]}

Toriyama, Miki ^{[1
]}

Tomioka, Kiyoshi ^{[1
,2
]}

机构：

[1] Doshisha Womens Coll Liberal Arts, Fac Pharmaceut Sci, Kyotanabe, Kyoto 6100395, Japan

[2] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Yoshida, Kyoto 6068501, Japan

[3] Maruho Co Ltd, Kyoto R&D Ctr, Translat Res Dept, Digital Translat Res Grp, Kyoto 6008815, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2024年 / 72卷 / 12期

关键词：

Key words hydroamination; aminolithiation; carbolithiation; tandem cyclization; tetrahydroprotoberberine; ALKALOIDS; CYCLIZATION; ALKYLLITHIUM;

D O I：

10.1248/cpb.c24-00693

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A total synthesis of javaberine A was achieved through a lithium amide-mediated intramolecular hydroamination of an N-allyl aminoalkene. The desired hydroamination was accomplished using an excess of i-Pr2NH with a substoichiometric amount of n-BuLi. Using an excess of both n-BuLi and i-Pr2NH led to tandem cyclization, however, resulting in the construction of a tricyclic structure through the formation of one C-N and two C-C bonds in a single operation. Additionally, epimerization of the H8-H14 cis-benzyl tetrahydroisoquinoline to the trans isomer was achieved via beta-elimination followed by intramolecular hydroamination.

引用

页码：1043 / 1047

页数：5

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