TY - JOUR A1 - Liu, Huili A1 - Zheng, Kuan A1 - Lu, Xiang A1 - Wang, Xiaoxia A1 - Hong, Ran T1 - Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy JF - Beilstein Journal of Organic Chemistry PY - 2013/// VL - 9 SP - 983 EP - 990 SN - 1860-5397 DO - 10.3762/bjoc.9.113 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.9.113 KW - alkene KW - desymmetrization KW - dioxygenation KW - lactone KW - PIFA KW - velbanamine N2 - A “stop-and-flow” strategy was developed for the chemoselective dioxygenation of alkenes with a PIFA-initiated cyclization. This method is conceived for the desymmetrization of seco-diene, and a series of substituted 5-hydroxymethyl-γ-lactones were constructed after hydrolysis. This strategy also differentiates terminally substituted alkenes and constitutes a potentially novel synthetic approach for the efficient synthesis toward velbanamine. ER -