Chiral Pool Guided Syntheses of Polycyclic Natural Products

Abstract

Comprehensive SummaryChiral pools have been commonly utilized as inexpensive and versatile building blocks in organic synthesis. In this account, we provide an overview of our recent synthetic efforts toward polycyclic natural products using chiral natural small molecules (chiral pool) as starting materials. Key achievements during our syntheses include intermolecular Diels‐Alder/intramolecular hetero‐Diels‐Alder cascade to enable modification of previously proposed biosynthetic pathway of bolivianine, Diels‐Alder‐type dimerization through a conjugated furanyl diene intermediate to achieve three types of lindenane [4+2] dimers, Iron‐catalyzed reductive aldol reaction to construct core of rumphellclovane E and [3,3]‐rearrangement along with vinylogous Pummerer rearrangement to make epoxyquinol substructure of JBIR‐23/‐24. In the final, the outlook is also presented. What is the most favorite and original chemistry developed in your research group?Biomimetic and/or convergent synthetic strategies leading to concise natural product synthesisHow do you get into this specific field? Could you please share some experiences with our readers?I have become interested in natural product synthesis (NPS) since I was a senior undergraduate student, encouraging me to enter this field in my PhD study. NPS is both fascinating and challenging to make complex molecules from simple starting materials, and construct different chemical bonds with proper stereochemistry. In my opinion, solid knowledge in reaction mechanism and structural conformation and persistent passion to pursue dreams are the two key elements aiming at successful and beautiful natural product synthesis.How do you supervise your students?Persuade them that it is important to be cautious with experiments, to be curious with new development and to be open with minds.What is the most important personality for scientific research?Passion, creativity, persistence and honesty.What are your hobbies?Music, reading and sight‐seeing.How do you keep balance between research and family?To tell the truth, I actually owe a lot to my family.