Issue 16, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of novel all-cis-functionalized cyclopropane template-assembled collagen models†

Shoko Yamazaki,*a   Mari Sakamoto,a   Michiko Suzuri,a   Masamitsu Doi,b   Takashi Nakazawac  and  Yuji Kobayashid  

* Corresponding authors

a Department of Chemistry, Nara University of Education, Takabatake-cho, Japan

b Department of Materials Science, Wakayama National College of Technology, Gobo, Japan

c Department of Chemistry, Nara Women's University, Japan

d Graduate School of Pharmaceutical Science, Osaka University, Suita, Japan

Abstract

An all-cis-functionalized cyclopropane template to connect the three peptide chains in a collagen model is designed. Stereoselective synthesis of cyclopropane-assembled collagen-model 2b with the minimum unit of Gly-Pro-Pro is based on a novel 1-seleno-2-silylethene [2 + 1] cycloaddition strategy. Reaction of the 1-seleno-2-silylethene 4 with triester-substituted olefin 5 in the presence of ZnI2 gives [2 + 1] cycloadduct 6 stereoselectively. Cyclopropane 6 is selectively transformed into triol 10 in four steps. The reaction of 10 and three equivalents of N-Boc-Pro-Pro-Gly-OH in the presence of WSC–DMAP and subsequent deprotection with TFA gives 2b.

Graphical abstract: Synthesis of novel all-cis-functionalized cyclopropane template-assembled collagen models

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Article information

DOI
https://doi.org/10.1039/B103887G
Article type
Paper
Submitted
01 May 2001
Accepted
20 Jun 2001
First published
31 Jul 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1870-1875

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Synthesis of novel all-cis-functionalized cyclopropane template-assembled collagen models

S. Yamazaki, M. Sakamoto, M. Suzuri, M. Doi, T. Nakazawa and Y. Kobayashi, J. Chem. Soc., Perkin Trans. 1, 2001, 1870 DOI: 10.1039/B103887G

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