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Topic: Cyclization to form polyheterocyclic compound  (Read 2841 times)

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Offline Rutherford

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Cyclization to form polyheterocyclic compound
« on: February 17, 2014, 05:35:54 AM »
What product will from in the cyclization reaction of the attached compound? I know that a nitrone moiety reacts in 1.3-dipolar cycloadditions, but what will add to it, as the product must have isoxazolidine and tetrahydrothiphene rings sharing a common bond (the two C atoms in the shared bond have S configuration, and the carbon connected to the oxygen has R configuration).

Offline discodermolide

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Re: Cyclization to form polyheterocyclic compound
« Reply #1 on: February 17, 2014, 05:37:45 AM »
If you are thinking cycloaddition of the nitrogen, the obvious partner is the acetylene.
See if that fits.
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Offline Rutherford

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Re: Cyclization to form polyheterocyclic compound
« Reply #2 on: February 17, 2014, 05:43:35 AM »
But that doesn't give the required condensed heterocycles that the product has: isoxazolidine and tetrahydrothiphene.

Offline discodermolide

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Re: Cyclization to form polyheterocyclic compound
« Reply #3 on: February 17, 2014, 06:01:40 AM »
How do you know the product contains these two heterocycles?
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Offline Rutherford

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Re: Cyclization to form polyheterocyclic compound
« Reply #4 on: February 17, 2014, 06:08:05 AM »
Here is the whole problem, without the historical background and the last part (E to F is the transformation I asked here). Maybe I mistaken with the initial compound:

Offline discodermolide

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Re: Cyclization to form polyheterocyclic compound
« Reply #5 on: February 17, 2014, 06:16:59 AM »
I really wish you would post the entire question instead of bits and pieces
Have a study of this document, on page 2 is the synthesis referred to.
http://www.scripps.edu/baran/images/grpmtgpdf/Shenvi_Aug_03.pdf

Perhaps you could also start to use Google to find things, as I did here.
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Offline Rutherford

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Re: Cyclization to form polyheterocyclic compound
« Reply #6 on: February 17, 2014, 07:04:05 AM »
In the reaction where SOCl2 is used, where does the ClCO2- moiety come from?

Offline discodermolide

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Re: Cyclization to form polyheterocyclic compound
« Reply #7 on: February 17, 2014, 07:37:14 AM »
I think the sulphur is missing.
Note the double inversion = retention of stereochemistry.
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Offline Rutherford

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Re: Cyclization to form polyheterocyclic compound
« Reply #8 on: February 17, 2014, 08:02:07 AM »
Yes. Thank you for the help.

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