Synthetic Studies on Multi-substituted Cyclopentane Natural Product, Pactamycin
- Synthetic Studies on Multi-substituted Cyclopentane Natural Product, Pactamycin
- 김태정; Yoko Saikawa; Masaya Nakata; 함정엽
- natural product; cyclopentane; pactamycin; bioactive compound
- Issue Date
- 2012 대한화학회 강원충북지부 광역 학술대회
- 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 aziridine 3, 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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