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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Total synthesis of (+)-lasonolide A
Tomoyuki Yoshimura1, Fumika Yakushiji, Shingo Kondo
1Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78 Sho-machi, Tokushima 770-8505, Japan.
Organic Letters
|January 27, 2006
Summary
Scientists achieved an enantiocontrolled total synthesis of (+)-lasonolide A. This was done using sequential cross metathesis and macrolactonization to construct the polyene macrolide core.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- (+)-Lasonolide A is a complex polyene macrolide with potential biological activities.
- The total synthesis of such complex natural products presents significant chemical challenges.
Purpose of the Study:
- To develop an enantiocontrolled total synthesis of (+)-lasonolide A.
- To establish efficient synthetic strategies for constructing the 20-membered polyene macrolide core.
Main Methods:
- Employing sequential cross-metathesis reactions for carbon-carbon bond formation.
- Utilizing macrolactonization as a key step for ring closure.
- Establishing stereochemical control throughout the synthesis.
Main Results:
- Successful enantiocontrolled total synthesis of (+)-lasonolide A.
- Efficient assembly of the 20-membered polyene macrolide core.
- Demonstration of the utility of sequential cross-metathesis and macrolactonization.
Conclusions:
- The developed synthetic route provides a viable pathway to (+)-lasonolide A.
- The strategy highlights the power of modern synthetic methodologies in natural product synthesis.
