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Enantioselective Synthesis of 3‐ Azabicyclo[4.3.0]nonane Alkaloids
Author(s) -
Cid Maria Magdalena,
PomboVillar Esteban
Publication year - 1993
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.19930760416
Subject(s) - chemistry , enantioselective synthesis , ketene , claisen rearrangement , piperidine , monoterpene , stereospecificity , stereochemistry , derivative (finance) , nonane , organic chemistry , economics , catalysis , financial economics
The stereospecific synthesis of the monoterpene alkaloids (−)‐α‐skytanthine ((−)‐ 2 ), (−)‐ N ‐demethyle‐δ‐sky‐tanthine((−)‐ 7 ), and (+)‐epidihydrotecomanine (+)‐ 4 was achieved from a common intermediate 22 , which in turn was obtained from (1 R ,4 S ,1′ S )‐2‐(1′‐phenylethyl)‐2‐azabicyclo[2.2.1]hept‐5‐ene (10) , via a ketene aza‐ Claisen rearrangement. The piperidine derivative (+)‐ 31 , formally the aza‐analogue of (+)‐isoiridomyrmecin, was also obtained from the same intermediate 22 .
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