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DOI: 10.1055/a-2103-9925
The Total Synthesis of Mollanol A by a Convergent Strategy
Financial Support was provided by the Major Project of the Department of Science and Technology of Gansu Province (22ZD6FA006), National Natural Science Foundation of China (21901094 and 22071089), and Lanzhou University
Abstract
Here, we briefly highlight our 15-step total synthesis of mollanol A, the first isolated member of the mollane-type grayanoids, which relied on a convergent strategy. A Stille coupling and a vinylogous aldol reaction/intramolecular oxa-Michael addition sequence were used to assemble the two fragments that featured most of the important chiral centers and nearly all the essential oxidation states of the natural product. The bicyclo[3.2.1]octane fragment was synthesized by using an InCl3-catalyzed Conia–ene cyclization reaction. The challenging tetrasubstituted alkene was constructed through a 1,4-reduction of the conjugated alkenes at a late stage.
1 Introduction
2 Total Synthesis of Mollanol A
3 Conclusion
Key words
grayanoids - total synthesis - mollanol A - convergent synthesis - Conia–ene cyclization - intramolecular oxa-Michael additionPublication History
Received: 22 May 2023
Accepted after revision: 31 May 2023
Accepted Manuscript online:
31 May 2023
Article published online:
10 July 2023
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