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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Total synthesis of (+)-13-deoxytedanolide
Lisa D Julian1, Jason S Newcom, William R Roush
1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Journal of the American Chemical Society
|April 28, 2005
Summary
This study details the total synthesis of 13-deoxytedanolide, overcoming challenges in hemiketal formation. A stereoselective aldol reaction successfully constructed the carbon skeleton, enabling the final product formation.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Tedanolide is a complex marine natural product with potential biological activities.
- Total synthesis provides access to complex molecules for further study and derivatization.
Purpose of the Study:
- To achieve the first total synthesis of 13-deoxytedanolide.
- To develop a stereoselective strategy for constructing the molecule's core structure.
Main Methods:
- A highly stereoselective fragment assembly aldol reaction was employed to build the carbon skeleton.
- Challenges related to hemiketal formation were addressed through a deoxygenation strategy.
Main Results:
- The complete carbon skeleton of 13-deoxytedanolide was successfully assembled.
- A key intermediate's hemiketal proved unreactive, necessitating a modification.
- Deoxygenation of the C(13)-hydroxyl group facilitated the final elaboration to 13-deoxytedanolide.
Conclusions:
- The total synthesis of 13-deoxytedanolide was successfully accomplished.
- The developed synthetic route provides a viable pathway to this complex natural product.
- The study highlights strategies for overcoming synthetic challenges in complex molecule synthesis.
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