Not sure how that winole23.dll will work in osx .

This may get you a little further :
http://macdevcenter.com/pub/a/mac/2007/02/27/replacing-applescript-with-ruby
.html?page=2

The other thought is to look into openoffice development tools.
http://downloadnew.org/scripts/text-management/openoffice-for-ruby-ooo4r-191
456.html

Cocoa stuff http://rubycocoa.sourceforge.net/HomePage

> From: Arti Singh <arti.p.singh / hotmail.com>
> Reply-To: <ruby-talk / ruby-lang.org>
> Newsgroups: comp.lang.ruby
> Date: Sat, 14 Aug 2010 04:41:08 +0900
> To: ruby-talk ML <ruby-talk / ruby-lang.org>
> Subject: Will ruby programs using win32ole run on  a Mac????
> 
> I have some ruby scripts that use win32ole to automate Microsoft Excel
> on Windows7, can I port this ruby script to my MAC and use it there?
> -- 
> Posted via http://www.ruby-forum.com/.
>