Following

./configure --prefix=$HOME/.local --with-assertions

and then running make leads to an error:

$ make
gcc -pthread -c -Wno-unused-result -Wsign-compare -g -fwrapv -O3 -Wall    -std=c99 -Wextra -Wno-unused-result -Wno-unused-parameter -Wno-missing-field-initializers -Werror=implicit-function-declaration  -I./Include/internal  -I. -I./Include    -DPy_BUILD_CORE -o Objects/codeobject.o Objects/codeobject.c
gcc -pthread -c -Wno-unused-result -Wsign-compare -g -fwrapv -O3 -Wall    -std=c99 -Wextra -Wno-unused-result -Wno-unused-parameter -Wno-missing-field-initializers -Werror=implicit-function-declaration  -I./Include/internal  -I. -I./Include    -DPy_BUILD_CORE -o Objects/complexobject.o Objects/complexobject.c
gcc -pthread -c -Wno-unused-result -Wsign-compare -g -fwrapv -O3 -Wall    -std=c99 -Wextra -Wno-unused-result -Wno-unused-parameter -Wno-missing-field-initializers -Werror=implicit-function-declaration  -I./Include/internal  -I. -I./Include    -DPy_BUILD_CORE -o Objects/descrobject.o Objects/descrobject.c
In file included from ./Include/object.h:746:0,
                 from ./Include/pytime.h:6,
                 from ./Include/Python.h:85,
                 from Objects/descrobject.c:3:
./Include/object.h:111:38: error: expected ‘)’ before ‘*’ token
 #define _PyObject_CAST(op) ((PyObject*)(op))
                                      ^
./Include/cpython/object.h:337:36: note: in definition of macro ‘PyType_HasFeature’
 #define PyType_HasFeature(t,f)  (((t)->tp_flags & (f)) != 0)
                                    ^
./Include/unicodeobject.h:115:18: note: in expansion of macro ‘PyType_FastSubclass’
                  PyType_FastSubclass(Py_TYPE(op), Py_TPFLAGS_UNICODE_SUBCLASS)
                  ^
./Include/object.h:122:34: note: in expansion of macro ‘_PyObject_CAST’
 #define Py_TYPE(ob)             (_PyObject_CAST(ob)->ob_type)
                                  ^
./Include/unicodeobject.h:115:38: note: in expansion of macro ‘Py_TYPE’
                  PyType_FastSubclass(Py_TYPE(op), Py_TPFLAGS_UNICODE_SUBCLASS)
                                      ^
./Include/unicodeobject.h:1042:56: note: in expansion of macro ‘PyUnicode_Check’
 #define _PyUnicode_CheckConsistency(op, check_content) PyUnicode_Check(op)
                                                        ^
./Include/internal/pycore_object.h:14:17: note: in expansion of macro ‘_PyUnicode_CheckConsistency’
 PyAPI_FUNC(int) _PyUnicode_CheckConsistency(PyObject *op, int check_content);
                 ^
./Include/object.h:111:40: error: expected ‘)’ before ‘(’ token
 #define _PyObject_CAST(op) ((PyObject*)(op))
                                        ^
./Include/cpython/object.h:337:36: note: in definition of macro ‘PyType_HasFeature’
 #define PyType_HasFeature(t,f)  (((t)->tp_flags & (f)) != 0)
                                    ^
./Include/unicodeobject.h:115:18: note: in expansion of macro ‘PyType_FastSubclass’
                  PyType_FastSubclass(Py_TYPE(op), Py_TPFLAGS_UNICODE_SUBCLASS)
                  ^
./Include/object.h:122:34: note: in expansion of macro ‘_PyObject_CAST’
 #define Py_TYPE(ob)             (_PyObject_CAST(ob)->ob_type)
                                  ^
./Include/unicodeobject.h:115:38: note: in expansion of macro ‘Py_TYPE’
                  PyType_FastSubclass(Py_TYPE(op), Py_TPFLAGS_UNICODE_SUBCLASS)
                                      ^
./Include/unicodeobject.h:1042:56: note: in expansion of macro ‘PyUnicode_Check’
 #define _PyUnicode_CheckConsistency(op, check_content) PyUnicode_Check(op)
                                                        ^
./Include/internal/pycore_object.h:14:17: note: in expansion of macro ‘_PyUnicode_CheckConsistency’
 PyAPI_FUNC(int) _PyUnicode_CheckConsistency(PyObject *op, int check_content);
                 ^
./Include/object.h:122:52: error: expected ‘)’ before ‘->’ token
 #define Py_TYPE(ob)             (_PyObject_CAST(ob)->ob_type)
                                                    ^
./Include/cpython/object.h:337:36: note: in definition of macro ‘PyType_HasFeature’
 #define PyType_HasFeature(t,f)  (((t)->tp_flags & (f)) != 0)
                                    ^
./Include/unicodeobject.h:115:18: note: in expansion of macro ‘PyType_FastSubclass’
                  PyType_FastSubclass(Py_TYPE(op), Py_TPFLAGS_UNICODE_SUBCLASS)
                  ^
./Include/unicodeobject.h:115:38: note: in expansion of macro ‘Py_TYPE’
                  PyType_FastSubclass(Py_TYPE(op), Py_TPFLAGS_UNICODE_SUBCLASS)
                                      ^
./Include/unicodeobject.h:1042:56: note: in expansion of macro ‘PyUnicode_Check’
 #define _PyUnicode_CheckConsistency(op, check_content) PyUnicode_Check(op)
                                                        ^
./Include/internal/pycore_object.h:14:17: note: in expansion of macro ‘_PyUnicode_CheckConsistency’
 PyAPI_FUNC(int) _PyUnicode_CheckConsistency(PyObject *op, int check_content);
                 ^
./Include/cpython/object.h:337:38: error: expected ‘)’ before ‘->’ token
 #define PyType_HasFeature(t,f)  (((t)->tp_flags & (f)) != 0)
                                      ^
./Include/object.h:351:35: note: in expansion of macro ‘PyType_HasFeature’
 #define PyType_FastSubclass(t,f)  PyType_HasFeature(t,f)
                                   ^
./Include/unicodeobject.h:115:18: note: in expansion of macro ‘PyType_FastSubclass’
                  PyType_FastSubclass(Py_TYPE(op), Py_TPFLAGS_UNICODE_SUBCLASS)
                  ^
./Include/unicodeobject.h:1042:56: note: in expansion of macro ‘PyUnicode_Check’
 #define _PyUnicode_CheckConsistency(op, check_content) PyUnicode_Check(op)
                                                        ^
./Include/internal/pycore_object.h:14:17: note: in expansion of macro ‘_PyUnicode_CheckConsistency’
 PyAPI_FUNC(int) _PyUnicode_CheckConsistency(PyObject *op, int check_content);
                 ^
./Include/cpython/object.h:337:56: error: expected ‘)’ before ‘!=’ token
 #define PyType_HasFeature(t,f)  (((t)->tp_flags & (f)) != 0)
                                                        ^
./Include/object.h:351:35: note: in expansion of macro ‘PyType_HasFeature’
 #define PyType_FastSubclass(t,f)  PyType_HasFeature(t,f)
                                   ^
./Include/unicodeobject.h:115:18: note: in expansion of macro ‘PyType_FastSubclass’
                  PyType_FastSubclass(Py_TYPE(op), Py_TPFLAGS_UNICODE_SUBCLASS)
                  ^
./Include/unicodeobject.h:1042:56: note: in expansion of macro ‘PyUnicode_Check’
 #define _PyUnicode_CheckConsistency(op, check_content) PyUnicode_Check(op)
                                                        ^
./Include/internal/pycore_object.h:14:17: note: in expansion of macro ‘_PyUnicode_CheckConsistency’
 PyAPI_FUNC(int) _PyUnicode_CheckConsistency(PyObject *op, int check_content);
                 ^
Makefile:1711: recipe for target 'Objects/descrobject.o' failed
make: *** [Objects/descrobject.o] Error 1

BTW, this happens even if Py_DEBUG=true is defined. System where the failure occurred: Ubuntu 16.04, 64-bit.