Synthetic Studies on Multi-substituted Cyclopentane Natural Product, Pactamycin

Title
Synthetic Studies on Multi-substituted Cyclopentane Natural Product, Pactamycin
Authors
김태정Yoko SaikawaMasaya Nakata함정엽
Keywords
natural product; cyclopentane; pactamycin; bioactive compound
Issue Date
2013-11
Publisher
2012 대한화학회 강원충북지부 광역 학술대회
Abstract
Pactamycin (1), an antitumor antibiotic produced by Streptomyces pactum var pactum[1], 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.[2] 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.
URI
http://pubs.kist.re.kr/handle/201004/46614
Appears in Collections:
KIST Publication > Conference Paper
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