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Total synthesis of (+)-sundiversifolide
Hiromasa Yokoe1, Hiroyuki Sasaki, Tomoyuki Yoshimura
1Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan.
Organic Letters
|February 14, 2007
Summary
The first enantiocontrolled total synthesis of (+)-sundiversifolide was achieved. Key steps included ring-closing metathesis, sigmatropic rearrangement, and iodolactonization to construct the natural product
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Sundiversifolide is a natural product with a complex cis-fused oxabicyclo[5.3.0]decene framework.
- Enantiocontrolled total synthesis is crucial for accessing complex natural products and their analogs for biological evaluation.
Purpose of the Study:
- To achieve the first enantiocontrolled total synthesis of (+)-sundiversifolide.
- To develop a synthetic strategy for constructing the core cis-fused oxabicyclo[5.3.0]decene skeleton.
Main Methods:
- Sequential application of key reactions including ring-closing metathesis.
- Utilization of a [3,3]-sigmatropic rearrangement for carbon-carbon bond formation.
- Employing iodolactonization as a crucial cyclization step.
Main Results:
- Successful enantiocontrolled total synthesis of (+)-sundiversifolide.
- Efficient assembly of the characteristic cis-fused oxabicyclo[5.3.0]decene framework.
Conclusions:
- The developed synthetic route provides access to (+)-sundiversifolide.
- The strategy highlights the utility of metathesis, sigmatropic rearrangement, and iodolactonization in complex natural product synthesis.
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