Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education College of Chemistry & Materials Science, Northwest University, Xi'an, 710127, China.
Angew Chem Int Ed Engl. 2019 Jun 3;58(23):7845-7849. doi: 10.1002/anie.201901651. Epub 2019 Apr 26.
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.
本文报道了伪海鞘素（1）和异海鞘素（2）的对映选择性全合成。通过 Carreira 的不对称双催化烯丙基化反应，在两个原始手性中心构建了优异的对映选择性和良好的非对映选择性，这为构建 1 和 2 的 C2 和 C3 处的非对映异构体提供了潜力。13 和 24 的阳离子环化反应为构建 1 和 2 中 C1 的相反构型提供了一种有效途径。此外，在 C4 处引入甲基的方法是对 1 和 2 中 C4 进行结构修饰的可行解决方案。
