Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy
- Resource Type
- article
- Authors
- Huili Liu; Kuan Zheng; Xiang Lu; Xiaoxia Wang; Ran Hong
- Source
- Beilstein Journal of Organic Chemistry, Vol 9, Iss 1, Pp 983-990 (2013)
- Subject
- alkene
desymmetrization
dioxygenation
lactone
PIFA
velbanamine
Science
Organic chemistry
QD241-441
- Language
- English
- ISSN
- 1860-5397
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.