Organic Letters
Organic Letters
5 years ago

Nazarov Cyclization Entry to Chiral Bicyclo[5.3.0]decanoid Building Blocks and Its Application to Formal Synthesis of (−)-Englerin A

Nazarov Cyclization Entry to Chiral Bicyclo[5.3.0]decanoid Building Blocks and Its Application to Formal Synthesis of (−)-Englerin A
Wen-Hua Chiou, Takahiro Koseki, Yoshiharu Iwabuchi, Yusuke Sasano, Keisuke Morisaki, Naoki Kanoh, Takuro Shibuta
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 β-alkoxy ketone with a zinc(II) ate complex.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02428

DOI: 10.1021/acs.orglett.7b02428

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