A convenient enantioselective synthesis of ( R )‐(−)‐phoracantholide I, a component of the defensive secretion of the eucalypt longicorn  Phoracantha synonyma | Zendy

Enders Dieter | Zendy; Plant Andrew | Zendy; Drechsel Karin | Zendy; Prokopenko Oleg F. | Zendy

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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.

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