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A convenient enantioselective synthesis of ( R )‐(−)‐phoracantholide I, a component of the defensive secretion of the eucalypt longicorn Phoracantha synonyma
Author(s) -
Enders Dieter,
Plant Andrew,
Drechsel Karin,
Prokopenko Oleg F.
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199506153
Subject(s) - enantioselective synthesis , chemistry , alkylation , hydrazone , secretion , component (thermodynamics) , ketone , stereochemistry , organic chemistry , biochemistry , catalysis , physics , thermodynamics
A short enantioselective synthesis of phoracantholide I [( R )‐ 4 ] (ee = 91 %), a component of the defensive secretion of the eucalypt longicorn Phoracantha synonyma , is described. Key steps of the synthesis are the enantioselective α‐alkylation of cyclononanone SAMP hydrazone [( S )‐ 1 ] (de > 93%) and subsequent Baeyer‐Villiger reaction of the ketone ( R )‐ 3 with retention of configuration.