1 research outputs found
Nazarov Cyclization Entry to Chiral BicycloÂ[5.3.0]Âdecanoid Building Blocks and Its Application to Formal Synthesis of (−)-Englerin A
A divergent entry
to the chiral bicyclo[5.3.0]Âdecane skeletons
relevant to sesqui- and higher terpenoids has been achieved. Its usefulness
was demonstrated by formal synthesis of a guaiane sesquiterpenoid
(−)-englerin A. The key reactions are (i) diastereoselective
Nazarov cyclization for stereoselective construction of the bicyclo[5.3.0]Âdecane
skeleton, (ii) intramolecular C–H amination for tuning an oxidation
state, and (iii) introduction of an alkyl group to a β-alkoxy
ketone with a zincÂ(II) ate complex