Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (−)-cylindrocyclophane A and its enantiomer, and implications for biological activity

Hiroyuki Yamakoshi; Fumiya Ikarashi; Masataka Minami; Masatoshi Shibuya; Tsutomu Sugahara; Naoki Kanoh; Hisatsugu Ohori; Hiroyuki Shibata; Yoshiharu Iwabuchi

doi:10.1039/B909646A

skip RSC | ChemSpider | Feedback

Home > Journals > Organic & Biomolecular ... > Syntheses of naturally ...

Authors & Referees | Librarians

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Organic & Biomolecular Chemistry

Issue 18, 2009

More about this Journal
Editorial Board
Submit an Article

Follow Journal | |

Journal Home | RSC Journals

Paper

Previous Article | Next Article

Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (−)-cylindrocyclophane A and its enantiomer, and implications for biological activity

Hiroyuki Yamakoshi , Fumiya Ikarashi , Masataka Minami , Masatoshi Shibuya , Tsutomu Sugahara , Naoki Kanoh , Hisatsugu Ohori , Hiroyuki Shibata and Yoshiharu Iwabuchi

Org. Biomol. Chem., 2009, 7, 3772-3781

DOI: 10.1039/B909646A
Received 15 May 2009, Accepted 16 Jun 2009
First published on the web 14 Jul 2009

Please wait while Download options loads

Request Permissions

Abstract
Cited by
Compounds
Related Content

The total syntheses of (−)-cylindrocyclophane A (1), a naturally occurring, cytotoxic [7.7]paracyclophane, and its enantiomer have been achieved in an enantiodivergent manner starting from a chiral propargyl alcohol building block using Smith's cross metathesis/ring-closing metathesis protocol as the key step. The biological evaluation of both enantiomers of cylindrocyclophane A (1 and ent-1) and its analogues indicated that the chirality of 1 is irrelevant to its cytotoxicity, which is attributed to the resorcinol motifs embedded in the robust [7.7]paracyclophane framework.

Abstract from Natural Product Updates 2010

No abstract available

This may take some time to load.

Supplementary Info

Synthetic methods and compound data
PDF (786K)
¹H- and ¹³C-NMR spectra
PDF (11624K)

Articles By

Hiroyuki Yamakoshi
Fumiya Ikarashi
Masataka Minami
Masatoshi Shibuya
Tsutomu Sugahara
Naoki Kanoh
Hisatsugu Ohori
Hiroyuki Shibata
Yoshiharu Iwabuchi

Terms & Conditions|Privacy |Accessibility|ACAP Enabled

Organic & Biomolecular Chemistry

Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (−)-cylindrocyclophane A and its enantiomer, and implications for biological activity

Log in (Free Access)

Log in (Subscriber Access)

Supplementary Info

Articles By