Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone
1997; Elsevier BV; Volume: 53; Issue: 48 Linguagem: Inglês
10.1016/s0040-4020(97)01014-4
ISSN1464-5416
AutoresA. B. Charette, Hélène Jûteau,
Tópico(s)Plant-derived Lignans Synthesis and Bioactivity
ResumoThe chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH2I)2 was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield.
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