opensslが古いとpythonのいろんなところに問題が出る ref: http://qiita.com/_akisato/items/4b531aab65de8cd2909a

file0.txt

# easy_install pip
Reading https://pypi.python.org/simple/pip/
Download error on https://pypi.python.org/simple/pip/: [Errno 1] _ssl.c:510: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed -- Some packages may not be found!
Couldn't retrieve index page for 'pip'
Scanning index of all packages (this may take a while)
Reading https://pypi.python.org/simple/
Download error on https://pypi.python.org/simple/: [Errno 1] _ssl.c:510: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed -- Some packages may not be found!
Best match: pip 6.0.6
Processing pip-6.0.6-py2.7.egg
pip 6.0.6 is already the active version in easy-install.pth
Installing pip script to /home/akisato/src/downloads/python-2.7.8/bin
Installing pip2.7 script to /home/akisato/src/downloads/python-2.7.8/bin
Installing pip2 script to /home/akisato/src/downloads/python-2.7.8/bin

Using /home/akisato/src/downloads/python-2.7.8/lib/python2.7/site-packages/pip-6.0.6-py2.7.egg

# pip install setuptools --upgrade
Could not find any downloads that satisfy the requirement setuptools in ./lib/python2.7/site-packages/setuptools-12.0.1-py2.7.egg
Collecting setuptools
  No distributions at all found for setuptools in ./lib/python2.7/site-packages/setuptools-12.0.1-py2.7.egg

file1.txt

# wget https://pypi.python.org/packages/source/p/pip/pip-6.0.6.tar.gz --check-no-certificate
# tar xzvf pip-6.0.6.tar.gz
# cd pip-6.0.6.tar.gz
# python setup.py build
# python setup.py install

file2.txt

# vim ~/src/downloads/python-2.7.6rc1/lib/python2.7/site-packages/pip-6.0.6-py2.7.egg/pip/downloads.py
Dispatch the actual request と書いてある行の次を，
return super(PipSession, self).request(method, url, verify=False, *args, **kwargs)
と書き換える。(verify=False を書き足す．) 

file3.txt

# pip install python
Collecting ipython
  Downloading ipython-2.3.1-py27-none-any.whl (2.8MB)
    100% |################################| 2.8MB 274kB/s
Installing collected packages: ipython

Successfully installed ipython-2.3.1