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Total Synthesis of (-)-Enigmazole A
Keisuke Sakurai1, Makoto Sasaki1, Haruhiko Fuwa2
1Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai, 980-8577, Japan.
Angewandte Chemie (International Ed. in English)
|February 23, 2018
Summary
The total synthesis of (-)-enigmazole A, a cytotoxic marine macrolide, was achieved. Key steps included domino olefin cross-metathesis and gold-catalyzed rearrangement for macrocycle formation.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Marine natural products are a rich source of bioactive compounds.
- (-)-Enigmazole A is a macrolide with demonstrated cytotoxic activity.
- The complex structure of (-)-enigmazole A presents a significant synthetic challenge.
Purpose of the Study:
- To achieve the total synthesis of (-)-enigmazole A.
- To develop novel synthetic strategies for constructing complex macrolides.
- To provide access to (-)-enigmazole A for further biological evaluation.
Main Methods:
- Domino olefin cross-metathesis/intramolecular oxa-Michael addition for tetrahydropyran construction.
- Gold-catalyzed rearrangement of a propargylic benzoate.
- Ring-closing metathesis for macrocyclization.
Main Results:
- Successful total synthesis of (-)-enigmazole A.
- Efficient construction of the tetrahydropyran core.
- Formation of the macrolide ring via a novel gold-catalyzed rearrangement and RCM.
Conclusions:
- The total synthesis of (-)-enigmazole A has been successfully accomplished.
- The developed synthetic route is efficient and highlights innovative methodologies.
- This synthesis opens avenues for exploring structure-activity relationships of marine macrolides.
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