RE: ORGLIST: Deprotection of the indole N

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From: will jones (willjones46$##$hotmail.com)
Date: Wed May 17 2006 - 10:53:34 EDT

Could you not get around the whole problem by constructing the indole ring
last? There are loads of ways to make an indol ring, or have you already
gone down that synthetic pathway as well?

>Dear Colleagues£¬
>
> Recently I was confused by the deprotection of the indole N. The
>protection
>group of the indole N is Bn, because of the ¦Á¦Âunsaturated carbonyl and
>another
>ester group in my molecular, it can¡¯t be deprotected by Na / NH3(l) and
>Pd / H2.
>I tried other methods from crossfire and scifinder (all kinds of lewis
>acid,;t-BuOK, DMSO; protonic acid; LDA), they all didn¡¯t work or made
>the
>substrate decompose. At this time, my boss suggest me change the Bn to
>PMB, but
>when I make it to PMB, I tried all the lewis acid, protonic acid , DDQ,
>CAN.
>Unfortunately, the reaction is also just like the Bn compound. Did
>someone know
>the other methods of deprotection of the Bn or PMB group at the indole
>N.
>
> Any suggestion will be welcome. Thank you for your attention and help!
>
>-Peng
>
>
>
>
>
>Peng Gao
>Prof. Xu Group
>National Laboratory of Applied Organic Chemistry
>(http://sklaoc.lzu.edu.cn/)
>Department of Chemistry, Lanzhou University
>Lanzhou P.R. China
>Email: pgao00$##$st.lzu.edu.cn
>
>
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