Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation

Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation

(−)-Deoxynupharidine has been synthesised via an intermediate that can also be used for other Nuphar alkaloids. Significant steps include the optimised enzymatic resolution of an allenic alcohol, highly diastereoselective silver-catalysed cyclisation of an allenic hydroxylamine, selective cross-meta...

Full description

Saved in:
Bibliographic Details
Main Authors: Bates, Roderick Wayland, Lim, Chia Juan, Collier, Steven J., Sukumaran, Joly
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2015
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/103835
http://hdl.handle.net/10220/25855
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Nanyang Technological University
Language: English
Description
Summary:(−)-Deoxynupharidine has been synthesised via an intermediate that can also be used for other Nuphar alkaloids. Significant steps include the optimised enzymatic resolution of an allenic alcohol, highly diastereoselective silver-catalysed cyclisation of an allenic hydroxylamine, selective cross-metathesis, diastereoselective intramolecular reductive amination, and stereoelectronically controlled enolate alkylation.

Similar Items