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Synlett 2017; 28(17): 2303-2306
DOI: 10.1055/s-0036-1588495
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© Georg Thieme Verlag Stuttgart · New York

Concise Synthesis of a Cyclopentane Intermediate Possessing All Nitrogen Functionalities for Pactamycin

Nobuyuki Matsumoto
Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan   Email: nisikawa@agr.nagoya-u.ac.jp
,
Atsuo Nakazaki
Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan   Email: nisikawa@agr.nagoya-u.ac.jp
,
Toshio Nishikawa*
Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan   Email: nisikawa@agr.nagoya-u.ac.jp
› Author AffiliationsThis work was supported by a Grant-in-Aid for Scientific Research (B) (No. 16H04915) and a Grant-in-Aid for Scientific Research on Innovative Areas ‘Chemical Biology of Natural Products’ (No. 23102015) from MEXT. N.M. thanks the Global COE program and the Program for Leading Graduate Schools: IGER Program in Green Natural Sciences from MEXT.
Further Information

Publication History

Received: 23 May 2017

Accepted after revision: 20 June 2017

Publication Date:
27 July 2017 (online)

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Dedicated to Prof. Dr. Volker Jäger

Abstract

Pactamycin, a potent antitumor and antimicrobial antibiotic, possesses a densely functionalized cyclopentane core structure. This paper describes the concise synthesis of an advanced intermediate for synthesizing the enantiomer of pactamycin that contains the cyclopentane skeleton bearing all the necessary amino functions with correct stereochemistries.

Key words

natural product synthesis - pactamycin - aminocyclopentitol - oxime–olefin cycloaddition - aziridines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588495.
  • Supporting Information
 

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