FULL PRODUCT VERSION :
java version "1.5.0_07"
Java(TM) 2 Runtime Environment, Standard Edition (build 1.5.0_07-b03)
Java HotSpot(TM) Client VM (build 1.5.0_07-b03, mixed mode, sharing)

ADDITIONAL OS VERSION INFORMATION :
Microsoft Windows 2000 [Versione 5.00.2195]

A DESCRIPTION OF THE PROBLEM :
javadoc exists with a classcastexception when trying to process annotations.

The stack trace is:

java.lang.ClassCastException: com.sun.tools.javadoc.ClassDocImpl
        at com.sun.tools.javadoc.AnnotationDescImpl.annotationType(AnnotationDescImpl.java:46)
        at com.sun.tools.doclets.internal.toolkit.util.Util.isDeprecated(Util.java:804)
        at com.sun.tools.doclets.formats.html.TagletWriterImpl.deprecatedTagOutput(TagletWriterImpl.java:70)
        at com.sun.tools.doclets.internal.toolkit.taglets.DeprecatedTaglet.getTagletOutput(DeprecatedTaglet.java:40)
        at com.sun.tools.doclets.formats.html.HtmlSerialFieldWriter.writeMemberDeprecatedInfo(HtmlSerialFieldWriter.java
:96)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.buildFieldInfo(SerializedFormBuilder.ja
va:444)
        at sun.reflect.GeneratedMethodAccessor140.invoke(Unknown Source)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:585)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.invokeMethod(SerializedFormBuilder.java
:131)
        at com.sun.tools.doclets.internal.toolkit.builders.AbstractBuilder.build(AbstractBuilder.java:90)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.buildSerializableFields(SerializedFormB
uilder.java:482)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:585)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.invokeMethod(SerializedFormBuilder.java
:131)
        at com.sun.tools.doclets.internal.toolkit.builders.AbstractBuilder.build(AbstractBuilder.java:90)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.buildClassSerializedForm(SerializedForm
Builder.java:185)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:585)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.invokeMethod(SerializedFormBuilder.java
:131)
        at com.sun.tools.doclets.internal.toolkit.builders.AbstractBuilder.build(AbstractBuilder.java:90)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.buildPackageSerializedForm(SerializedFo
rmBuilder.java:167)
        at sun.reflect.GeneratedMethodAccessor138.invoke(Unknown Source)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:585)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.invokeMethod(SerializedFormBuilder.java
:131)
        at com.sun.tools.doclets.internal.toolkit.builders.AbstractBuilder.build(AbstractBuilder.java:90)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.buildSerializedFormSummaries(Serialized
FormBuilder.java:148)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:585)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.invokeMethod(SerializedFormBuilder.java
:131)
        at com.sun.tools.doclets.internal.toolkit.builders.AbstractBuilder.build(AbstractBuilder.java:90)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.buildSerializedForm(SerializedFormBuild
er.java:116)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:585)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.invokeMethod(SerializedFormBuilder.java
:131)
        at com.sun.tools.doclets.internal.toolkit.builders.AbstractBuilder.build(AbstractBuilder.java:90)
        at com.sun.tools.doclets.internal.toolkit.builders.SerializedFormBuilder.build(SerializedFormBuilder.java:101)
        at com.sun.tools.doclets.internal.toolkit.AbstractDoclet.generateOtherFiles(AbstractDoclet.java:137)
        at com.sun.tools.doclets.formats.html.HtmlDoclet.generateOtherFiles(HtmlDoclet.java:66)
        at com.sun.tools.doclets.internal.toolkit.AbstractDoclet.startGeneration(AbstractDoclet.java:122)
        at com.sun.tools.doclets.internal.toolkit.AbstractDoclet.start(AbstractDoclet.java:64)
        at com.sun.tools.doclets.formats.html.HtmlDoclet.start(HtmlDoclet.java:42)
        at com.sun.tools.doclets.standard.Standard.start(Standard.java:23)
        at gr.spinellis.umlgraph.doclet.UmlDoc.start(UmlDoc.java:48)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:39)
        at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
        at java.lang.reflect.Method.invoke(Method.java:585)
        at com.sun.tools.javadoc.DocletInvoker.invoke(DocletInvoker.java:269)
        at com.sun.tools.javadoc.DocletInvoker.start(DocletInvoker.java:143)
        at com.sun.tools.javadoc.Start.parseAndExecute(Start.java:340)
        at com.sun.tools.javadoc.Start.begin(Start.java:128)
        at com.sun.tools.javadoc.Main.execute(Main.java:41)
        at com.sun.tools.javadoc.Main.main(Main.java:31)


The bug is triggered by two tools I know of, maven and annogen, when runnig the standard doclet (so, not from command line, but from an external application that calls com.sun.tools.javadoc.Main.
Unfortunately I don't have a test case for it, but you can refer to the associated bug reports on the maven and annogen issue trackers:

http://jira.codehaus.org/browse/ANNOGEN-14
http://jira.codehaus.org/browse/MJAVADOC-72


REPRODUCIBILITY :
This bug can be reproduced always.