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An Enantioselective Total Synthesis of Natural (+)‐Luciduline
Author(s) -
Oppolzer Wolfgang,
Petrzilka Martin
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610802
Subject(s) - chemistry , enantioselective synthesis , regioselectivity , intramolecular force , total synthesis , nitrone , yield (engineering) , sequence (biology) , stereochemistry , lycopodium , organic chemistry , catalysis , cycloaddition , biochemistry , materials science , metallurgy
The naturally occurring Lycopodium alkaloid (+)‐luciduline ( 1 ) has been synthesized from ( R )‐5‐methyl‐cyclohex‐2‐en‐1‐one ( 12 ) by a sequence of seven steps (s. Scheme 6 ) in 33% overall yield. The key step 4→6 presumably involves a transient nitrone 5 which undergoes a highly regioselective intramolecular addition to a non‐polarized olefinic bond.