Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China.
Org Lett. 2010 Dec 3;12(23):5366-9. doi: 10.1021/ol101922h. Epub 2010 Nov 9.
An expedient diastereoselective synthesis of highly functionalized indolo[2,3-α]quinolizidines adopting a cis H2/H12b geometry has been realized by a Pictet-Spengler/lactamization cascade sequence. The absolute stereochemistry at C2, C3, and C12b was governed by the originally created chirality of the Michael adduct through organocatalyzed conjugate addition of dialkyl malonates to α,β-unsaturated aldehydes.
通过Pictet-Spengler/环化级联序列，实现了一种采用顺式 H2/H12b 几何构型的高度官能化吲哚并[2,3-α]喹啉啶的简便非对映选择性合成。C2、C3 和 C12b 的绝对立体化学由最初通过二烷基丙二酸酯与α,β-不饱和醛的有机催化共轭加成产生的迈克尔加成物的手性控制。
