Studies toward the total synthesis of Octa-substituted Cyclopentane Natural Product, Pactamycin
- Studies toward the total synthesis of Octa-substituted Cyclopentane Natural Product, Pactamycin
- 김태정; 요코 사이카와; 마사야 나카타; 함정엽
- Cyclopentane; Natural Product; Pactamycin; total synthesis; heterocycle; oxazoline; azidirine; ring-closing metathesis
- Issue Date
- 2011년 대한화학회 강원/충북 추계 광역지부회
- Pactamycin (1), an antitumor antibiotic produced by Streptomyces pactum var pactum, was isolated in 1962 and is one of the most potent cytotoxic agents in vitro against KB human epidermoid carcinoma cells and inhibits the synthesis of specific proteins. Pactamycin (1) has a unique octa-substituted cyclopentane ring whose all carbons are substituted by heteroatoms. As a part of the project directed towards the total synthesis of pactamycin (1), we designed aziridine3, potentially functionalized for further conversion into 1.
The construction of the pactamycin carbon framework started with Seebach oxazoline 2, which was converted into azidirine 3 in 12 steps including Grubbs ring-closing metathesis and stereoselective aziridine formation. Further studies toward the intermediate having a highly functionalized cyclopentane ring from aziridine 3 are now in progress and will be disclosed.
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