A Radical-Based Synthesis of Lingzhiol

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Medicinal Chemistry

Background:

• Lingzhiol is a complex polycyclic natural product with potential biological activities.
• Efficient synthetic routes are crucial for studying and developing natural products.

Purpose of the Study:

• To develop a novel and efficient synthetic strategy for lingzhiol.
• To synthesize lingzhiol and a key analogue for further investigation.

Main Methods:

• Total synthesis of lingzhiol and an analogue.
• Utilized benzylic radical cyclization of a spiroepoxide intermediate.
• Key steps included oxidative cleavage and diastereoselective reduction.

Main Results:

• Successfully synthesized lingzhiol [(±)-1] from dimethoxytetralone 8.
• Constructed the tetracyclic core via radical cyclization onto an alkynyl substituent.
• Synthesized lingzhiol analogue 39 from 5-methoxy-1-tetralone (27).

Conclusions:

• The developed synthetic route provides access to lingzhiol and its analogues.
• The strategy highlights the utility of benzylic radical cyclization in complex molecule synthesis.