Facile Method for Stereoselective Synthesis of New Chiral (1R,4aR,8aR)‐1,3,4,4a,5,7,8,8a‐Octahydro‐2‐methylene‐naphthalene‐6‐one‐1‐propanenitrile, an Important Precursor of Solanapyrones

Abstract

A novel and facile strategy for stereoselective synthesis of new chiral (1R,4aR,8aR)‐1,3,4,4a,5,7,8,8a‐octahydro‐2‐methylenenaphthalene‐6‐one‐1‐propanenitrile (8) by one‐pot stereoselective hydrogenation/acetalization and Beckmann fragmentation is described. Chiral octalone 8, an important precursor of solanapyrone, was obtained in good yield.

The crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication No. CCDC 249552.

Keywords:

• Beckmann fragmentation
• chiral octalone
• one‐pot hydrogenation/acetalization
• stereoselective synthesis

Acknowledgments

The author is grateful to Professor Yuefei Hu and Professor Hongwen Hu for their guidance. The author is also grateful for the financial support from the Natural Science Foundation of Educational Committee of Jiangsu Province, P.R. China (No. 05KJB-150039).

Notes

The crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication No. CCDC 249552.