1.
Org Lett
; 19(19): 5142-5145, 2017 10 06.
Artigo
em Inglês
| MEDLINE
| ID: mdl-28952739
RESUMO
A divergent entry to the chiral bicyclo[5.3.0]decane 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]decane skeleton, (ii) intramolecular C-H amination for tuning an oxidation state, and (iii) introduction of an alkyl group to a ß-alkoxy ketone with a zinc(II) ate complex.