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Synthesis of (−)‐Deoxynupharidine by Allenic Hydroxylamine Cyclisation
Author(s) -
Bates Roderick W.,
Lim Chia Juan,
Collier Steven J.,
Sukumaran Joly
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500094
Subject(s) - chemistry , hydroxylamine , reductive amination , amination , intramolecular force , alkylation , metathesis , alcohol , organic chemistry , stereochemistry , catalysis , polymerization , polymer
Abstract (−)‐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.