diff --git a/Lib/distutils/sysconfig.py b/Lib/distutils/sysconfig.py
index ac06313..16902ca 100644
--- a/Lib/distutils/sysconfig.py
+++ b/Lib/distutils/sysconfig.py
@@ -146,6 +146,7 @@
             "I don't know where Python installs its library "
             "on platform '%s'" % os.name)
 
+_USE_CLANG = None
 
 def customize_compiler(compiler):
     """Do any platform-specific customization of a CCompiler instance.
@@ -158,8 +159,38 @@
             get_config_vars('CC', 'CXX', 'OPT', 'CFLAGS',
                             'CCSHARED', 'LDSHARED', 'SO', 'AR', 'ARFLAGS')
 
+        newcc = None
         if 'CC' in os.environ:
-            cc = os.environ['CC']
+            newcc = os.environ['CC']
+        elif sys.platform == 'darwin' and cc == 'gcc-4.2':
+            # Issue #13590:
+            #       Since Apple removed gcc-4.2 in Xcode 4.2, we can no
+            #       longer assume it is available for extension module builds.
+            #       If Python was built with gcc-4.2, check first to see if
+            #       it is available on this system; if not, try to use clang
+            #       instead unless the caller explicitly set CC.
+            global _USE_CLANG
+            if _USE_CLANG is None:
+                from distutils import log
+                from subprocess import Popen, PIPE
+                p = Popen("! type gcc-4.2 && type clang && exit 2",
+                                shell=True, stdout=PIPE, stderr=PIPE)
+                p.wait()
+                if p.returncode == 2:
+                    _USE_CLANG = True
+                    log.warn("gcc-4.2 not found, using clang instead")
+                else:
+                    _USE_CLANG = False
+            if _USE_CLANG:
+                newcc = 'clang'
+        if newcc:
+            # On OS X, if CC is overridden, use that as the default
+            #       command for LDSHARED as well
+            if (sys.platform == 'darwin'
+                    and 'LDSHARED' not in os.environ
+                    and ldshared.startswith(cc)):
+                ldshared = newcc + ldshared[len(cc):]
+            cc = newcc
         if 'CXX' in os.environ:
             cxx = os.environ['CXX']
         if 'LDSHARED' in os.environ:
diff --git a/Misc/NEWS b/Misc/NEWS
index d1f9ab0..da90e9e 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -113,6 +113,19 @@
 Library
 -------
 
+- Issue #13590: On OS X 10.7 and 10.6 with Xcode 4.2, building
+  Distutils-based packages with C extension modules may fail because
+  Apple has removed gcc-4.2, the version used to build python.org
+  64-bit/32-bit Pythons.  If the user does not explicitly override
+  the default C compiler by setting the CC environment variable,
+  Distutils will now attempt to compile extension modules with clang
+  if gcc-4.2 is required but not found. Also as a convenience, if
+  the user does explicitly set CC, substitute its value as the default
+  compiler in the Distutils LDSHARED configuration variable for OS X.
+  (Note, the python.org 32-bit-only Pythons use gcc-4.0 and the 10.4u
+  SDK, neither of which are available in Xcode 4.  This change does not
+  attempt to override settings to support their use with Xcode 4.)
+
 - Issue #13960: HTMLParser is now able to handle broken comments when
   strict=False.