You can create outlines using
Text Speaker. While reading your file, you can mark important sections of your e-book for outlining. Later, you can have Text Speaker read aloud the marked areas, or convert the marked text into an audio file.
Select the text for audio outline and click Edit menu >> Outline Area. The outlined text is shown with a yellow background and is enclosed within the tags <OUTLINED> and </OUTLINED>.
To listen to the marked text, click Speak menu >> Speak Outlined Text. Convert the marked text to an audio file by clicking Speak menu >> Convert Outlined Text and you will have a file of your key points you can listen to on your iPod.