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An approach to (±)-Lingzhiol.

Xiaoyu Li¹, Xiaoyu Liu¹, Xiaozhen Jiao¹

¹State Key Laboratory of Bioactive Substance and Function of Natural Medicine, Beijing Key Laboratory of Active Substance Discovery and Drugability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , No. 1 Xiannongtan Street, Beijing 100050, China.

Organic Letters

|April 5, 2016

Summary

Researchers synthesized (±)-Lingzhiol using a novel seven-step process. This method features an acid-catalyzed semipinacol-type rearrangement, yielding the tetracyclic core structure efficiently.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Lingzhiol is a complex tetracyclic molecule.
Efficient synthesis of complex natural products is a key challenge in organic chemistry.

Purpose of the Study:

To develop a novel and efficient synthetic route for (±)-Lingzhiol.
To establish a new strategy for constructing the 5/5/6/6 tetracyclic core.

Main Methods:

Multi-step synthesis starting from 5,8-dimethoxytetralone.
Utilized an unprecedented acid-catalyzed semipinacol-type rearrangement.
Employed a tandem rearrangement/reduction/lactonization sequence.

Main Results:

Achieved a seven-step synthesis of (±)-Lingzhiol.

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Obtained an overall yield of 10.3%.

Successfully constructed the tetracyclic 5/5/6/6 core structure.

Conclusions:

The developed synthetic route is efficient for accessing (±)-Lingzhiol.
The novel tandem reaction strategy provides a powerful tool for building complex polycyclic systems.