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Published April 28, 2024
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Convenient access to a strained bicyclic enone: A concise and improved formal synthesis of ineleganolide
Abstract
The norcembranoid and cembranoid diterpenoids represent an intriguing class of natural products isolated from marine sources. Their chemical synthesis has been a challenging and exciting field of research over the past two decades, owing largely to their structural complexity. We recently disclosed a total synthesis of a member of this class, ineleganolide, in a 23 step longest linear sequence. In search of a shorter, more efficient route, we have devised a new strategy for the synthesis of a key bicyclic enone. Disclosed herein is our improved synthesis of this strained intermediate, completing the formal synthesis of ineleganolide in only 14 steps, thereby shortening our previous synthesis by 9 steps.
Copyright and License
© 2024 Elsevier.
Acknowledgement
We thank the NIH (R35 GM 145239), the Heritage Medical Research Investigator Program, and Caltech for financial support.
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Conflict of Interest
Brian M. Stoltz is the Editor in Chief of Tetrahedron, the sister journal of Tetrahedron Letters. The authors declare that they have no otherwise known competing financial interests that could have appeared to influence the research reported in this paper.
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Funding
- National Institutes of Health
- R35GM145239
- California Institute of Technology
- Heritage Medical Research Institute