Enantioselective Total Synthesis of Pseudopteroxazole and Ileabethoxazole

被引：18

作者：

Zhang, Xuan ^{[1
]}

Fang, Xianhe ^{[1
]}

Xu, Miao ^{[1
]}

Lei, Yibo ^{[1
]}

Wu, Zibo ^{[1
]}

Hu, Xiangdong ^{[1
]}

机构：

[1] Northwest Univ, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Coll Chem & Mat Sci, Xian 710127, Shaanxi, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 23期

基金：

美国国家科学基金会;

关键词：

asymmetric synthesis; cyclization; natural products; total synthesis; ASYMMETRIC TOTAL-SYNTHESIS; ALPHA-ALLYLATION; REVISION; BENZOTHIAZINES; IRIDIUM; ROUTE;

D O I：

10.1002/anie.201901651

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective total syntheses of pseudopteroxazole (1) and ileabethoxazole (2) are presented. The two original stereocenters were constructed in excellent enantioselectivity and good diastereoselectivity through Carreira's asymmetric dual catalytic allylation, which shows potential for accessing diastereoisomers at C2 and C3 of 1 and 2. Cationic cyclizations of 13 and 24 demonstrated an effective pathway for the construction of the opposite configurations at C1 in 1 and 2. Additionally, an approach for the introduction of methyl at C4 is a feasible solution for structural modifications at C4 in 1 and 2.

引用

页码：7845 / 7849

页数：5

共 34 条

[31] Enantioselective Total Syntheses of Various Amphilectane and Serrulatane Diterpenoids via Cope Rearrangements [J].