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Total synthesis of (+)-Brefeldin A
Young-Ger Suh1, Jae-Kyung Jung, Seung-Yong Seo
1College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Kwanak-Gu 151-742, Korea. ygsuh@plaza.snu.ac.kr
The Journal of Organic Chemistry
|June 11, 2002
Summary
The total synthesis of (+)-brefeldin A was achieved in 15 steps. This study highlights a novel method for constructing the hydroxycyclopentane core and introducing the acrylate side chain.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Natural Product Synthesis
Background:
- (+)-Brefeldin A is a potent biologically active natural product.
- Efficient synthetic routes are crucial for accessing complex molecules like (+)-brefeldin A.
Purpose of the Study:
- To achieve the total synthesis of (+)-brefeldin A.
- To develop a novel synthetic strategy for constructing key structural features.
Main Methods:
- A 15-step linear synthesis was employed.
- Stereoselective construction of a cis-disubstituted hydroxycyclopentane skeleton.
- Introduction of the C1-C3 acrylate moiety using a trans-vinylogous acyl anion equivalent.
Main Results:
- The total synthesis of (+)-brefeldin A was successfully completed.
- An overall yield of 7.9% was achieved from Weinreb amide 6.
- A new variant of a trans-vinylogous acyl anion equivalent was utilized.
Conclusions:
- The developed synthetic route is effective for (+)-brefeldin A.
- The novel methodology enables efficient stereoselective synthesis.
- This work provides a valuable pathway for brefeldin A analogs.