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Using the configure options {{{--enable-shared --enable-pthread --without-tk}}} on OS X 10.4.11, build fails.
This is the tail of the make output:

{{{
 cc -dynamic -bundle -undefined suppress -flat_namespace -o
 ../../../../.ext/i386-darwin8/json/ext/parser.bundle parser.o unicode.o
 -L. -L../../../.. -L. -L/opt/local/lib    -lruby1.9  -lpthread -ldl -lobjc
 compiling mathn/complex
 mkdir -p ../../../.ext/i386-darwin8/mathn
 /usr/bin/gcc-4.0 -I. -I../../../.ext/include/i386-darwin8
 -I../../.././include -I../../.././ext/mathn/complex
 -DRUBY_EXTCONF_H=\"extconf.h\" -DEXT_MATHN -DCANON -DCLCANON  -fno-common
 -O2 -O2 -g -Wall -Wno-parentheses  -fno-common -pipe -fno-common  -o
 complex.o -c complex.c
 cc -dynamic -bundle -undefined suppress -flat_namespace -o
 ../../../.ext/i386-darwin8/mathn/complex.bundle complex.o -L. -L../../..
 -L. -L/opt/local/lib    -lruby1.9  -lpthread -ldl -lobjc
 /usr/bin/ld: multiple definitions of symbol _rb_complex_raw
 complex.o definition of _rb_complex_raw in section (__TEXT,__text)
 ../../../libruby1.9.dylib(complex.o) definition of _rb_complex_raw
 /usr/bin/ld: multiple definitions of symbol _rb_complex_polar
 complex.o definition of _rb_complex_polar in section (__TEXT,__text)
 ../../../libruby1.9.dylib(complex.o) definition of _rb_complex_polar
 /usr/bin/ld: multiple definitions of symbol _rb_complex_new
 complex.o definition of _rb_complex_new in section (__TEXT,__text)
 ../../../libruby1.9.dylib(complex.o) definition of _rb_complex_new
 /usr/bin/ld: multiple definitions of symbol _rb_Complex
 complex.o definition of _rb_Complex in section (__TEXT,__text)
 ../../../libruby1.9.dylib(complex.o) definition of _rb_Complex
 collect2: ld returned 1 exit status
 make[1]: *** [../../../.ext/i386-darwin8/mathn/complex.bundle] Error 1
 make: *** [exts] Error 1
}}}

Built on 10.4.11/Intel, build throught MacPorts.

See mp ticket for comparison: http://trac.macports.org/ticket/17177