ORGLIST: References Sought

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From: Darren Rhodes (drhodes$##$
Date: Wed Feb 07 2001 - 17:18:14 EST

I posted this message to sci.chem a couple of days ago but I haven't had
a response yet (the signal to noise ratio of that group is nearly less
than one at the moment). Perhaps someone here can help; also, since the
group has been discussing pictorial representations of molecules etc the
email may be of interest with that regard.

I'm looking for references to the chemistry described below - I'm
familiar with the modern references (eg paclitaxel side chain
epimerisation) but are there any older references out there? I'm
convinced that this chemistry is quite old; can anyone give me
references to support this conviction?

Converting the OH of [R1][C@@H](O)CNC([R2])=O to a suitable leaving
group (eg mesylate) followed by base treatment gives [R1]C1CN=C([R2])O1
(stereochem at this step omitted but this is where the inversion
occurs); hydrolysis of this compound gives [R1][C$##$H](O)CNC([R2])=O.

Thanks for any answers


ps I got the SMILES strings from
The site has a free
download section for applets etc ... I downloaded the
java script and
used it in Netscape Navigator to generate the SMILES
strings. I also
double checked the strings by pasting them back into
the Navigator
window (it will be apparent to you after downloading
and installing etc

pps This email isn't just an excuse to use SMILES - I
am interested in
the requested references.

ORGLIST - Organic Chemistry Mailing List
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List coordinator: Joao Aires de Sousa (jas$##$

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