Premium
A Concise Synthesis of (−)‐Indolizidines 209D and 209B
Author(s) -
WU Hao,
YU Menglong,
ZHANG Yazhu,
ZHAO Gang
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990015
Subject(s) - chemistry , indolizidine , aldehyde , ketone , stereoselectivity , bicyclic molecule , substrate (aquarium) , methyl ketone , stereochemistry , combinatorial chemistry , organic chemistry , alkaloid , catalysis , oceanography , geology
A general stereoselective synthetic route to 5‐substituted and 5,8‐disubstituted indolizidine alkaloids has been developed starting from commercially available L ‐proline. (−)‐Indolizidines 209D and 209B were efficiently synthesized in 9.8% and 14.8% overall yields in seven and five‐step reactions from readily available aldehyde 3 and ketone 10 , respectively. The key steps of this synthesis involve a substrate‐induced asymmetric addition of ethyl lithiopropiolate to aldehyde 3 or methyl ketone 10 , and a two‐step one‐pot hydrogenation/cyclization sequence to construct the bicyclic skeleton.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom