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Topic: Complicated reaction in jasmonate synthesis  (Read 2478 times)

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Offline Rutherford

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Complicated reaction in jasmonate synthesis
« on: February 17, 2014, 12:10:59 PM »
What is happening in the attached reaction?
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Offline discodermolide

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Re: Complicated reaction in jasmonate synthesis
« Reply #1 on: February 17, 2014, 12:14:34 PM »
Read the publication!
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Offline Rutherford

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Re: Complicated reaction in jasmonate synthesis
« Reply #2 on: February 17, 2014, 12:16:51 PM »
The compound 6 isn't the same they wrote afterwards, or is it?
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Offline Rutherford

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Re: Complicated reaction in jasmonate synthesis
« Reply #3 on: February 17, 2014, 12:21:25 PM »
This compound 6 isn't the same as the one before.
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Offline Rutherford

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Re: Complicated reaction in jasmonate synthesis
« Reply #4 on: February 17, 2014, 12:36:06 PM »
I found out that the compound 6 in my first post is the correct one, but again, how is it produced ? What is the mechanism? In the publication they explain how the other compound 6 is produced.
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Offline discodermolide

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Re: Complicated reaction in jasmonate synthesis
« Reply #5 on: February 17, 2014, 12:42:26 PM »
Both compounds are the same:
O=C1OC2C3C1C4C(C3)C24
and
O=C(O1)C2C3C4CC2C1C34
both are
hexahydro-2H-3,5,6-(epimethanetriyl)cyclopentafuran-2-one
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Offline Rutherford

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Re: Complicated reaction in jasmonate synthesis
« Reply #6 on: February 17, 2014, 01:33:32 PM »
Okay, that led only to confusion.
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Offline Rutherford

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Re: Complicated reaction in jasmonate synthesis
« Reply #7 on: February 17, 2014, 01:47:56 PM »
I can't finish with their space arrangement of the molecule, so I would like to continue with the molecule drawn as in the mechanism. Which bond will be broken when HI is added to the attached compound?
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Offline Rutherford

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Re: Complicated reaction in jasmonate synthesis
« Reply #8 on: February 17, 2014, 02:13:39 PM »
I figured it out at the end. Thanks again.
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