I found a similar problem described in:
http://groups.google.com/group/sdruby/browse_thread/thread/d3ba3a487714bdb4?pli=1

I installed build-essential ruby-dev 4.2 libruby1.8-dbg  and retried
'sudo gem install rub-debug' after this, the gem installed correctly.

I suggest that there are missing dependencies on the ruby-gems package.

Cheers....

-- 
rubygems1.8 does not work - apppears misconfigured
https://bugs.launchpad.net/bugs/591575
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Status in “libgems-ruby” package in Ubuntu: New

Bug description:
I installed ruby 4.5, and rubygems1.8 from the Synaptic Package Manager, and 
tried to do
  sudo gem install ruby-debug, and am getting error messages that are beyond my 
capacity to fix.  The transcript from the terminal follows:

myu...@diglit-desktop:~$ ruby --version
ruby 1.8.7 (2010-01-10 patchlevel 249) [i486-linux]
myu...@diglit-desktop:~$ sudo gem install ruby-debug
[sudo] password for myuser: 
Building native extensions.  This could take a while...
ERROR:  Error installing ruby-debug:
        ERROR: Failed to build gem native extension.

/usr/bin/ruby1.8 extconf.rb
extconf.rb:1:in `require': no such file to load -- mkmf (LoadError)
        from extconf.rb:1


Gem files will remain installed in /var/lib/gems/1.8/gems/linecache-0.43 for 
inspection.
Results logged to /var/lib/gems/1.8/gems/linecache-0.43/ext/gem_make.out
myu...@diglit-desktop:~$

ProblemType: Bug
DistroRelease: Ubuntu 10.04
Package: rubygems (not installed)
ProcVersionSignature: Ubuntu 2.6.32-22.36-generic 2.6.32.11+drm33.2
Uname: Linux 2.6.32-22-generic i686
Architecture: i386
Date: Wed Jun  9 14:15:12 2010
InstallationMedia: Ubuntu 10.04 LTS "Lucid Lynx" - Release i386 (20100429)
ProcEnviron:
 LANG=en_AU.utf8
 SHELL=/bin/bash
SourcePackage: libgems-ruby





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