Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

A Radical-Based Synthesis of Lingzhiol

A Radical-Based Synthesis of Lingzhiol
Lea-Marina Mehl, Martin E. Maier
The polycyclic natural product lingzhiol [(±)-1] was synthesized from dimethoxytetralone 8 via cyclization of an intermediate benzylic radical, generated from spiroepoxide 14, onto an alkynyl substituent generating tetracyclic compound 13 with an exocyclic double bond. After oxidative cleavage of the double bond of 13 and reduction of the keto function of 23, the correct diastereomer, 12-syn, was converted to lingzhiol (1) via known steps. In a similar manner, lingzhiol analogue 39 was synthesized from 5-methoxy-1-tetralone (27).

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01416

DOI: 10.1021/acs.joc.7b01416

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