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Stereoselective Syntheses of (+)‐Broussonetine D and (+)‐Australine via a Functionalized Pyrrolidine from an Extended Chiral 1,3‐Oxazine
Author(s) -
Myeong InSoo,
Ham WonHun
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801552
Subject(s) - pyrrolidine , chemistry , stereoselectivity , yield (engineering) , aldehyde , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , materials science , metallurgy
The asymmetric syntheses of (+)‐broussonetine D and (+)‐australine have been achieved via a functionalized pyrrolidine obtained from an extended chiral 1,3‐oxazine. The key steps include pyrrolidine formation by oxazine cleavage and diastereoselective allylation to a pyrrolidine aldehyde. (+)‐Broussonetine D and (+)‐australine were synthesized from anti , syn , syn ‐oxazine, in six steps, with an overall yield of 22.2 %, and in seven steps, with an overall yield of 33.2 %.