A negative look-ahead is fine, just move the .* into the assertion.
if ($s =~ /^a(?!.*ab).*b$/) {
Cheers, JohnGG
Update: If you want "a00000000ab" to match then you could change the look-ahead to ensure there is at least one character after the "ab".
use strict;
use warnings;
my @strings = qw{
a000000000b
a0a0000b00b
a0000ab000b
a00000000ab
};
print
m{^a(?!.*ab.).*b$}
? qq{$_: matched\n}
: qq{$_: unmatched\n}
for @strings;
which produces
a000000000b: matched
a0a0000b00b: matched
a0000ab000b: unmatched
a00000000ab: matched
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