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Topic: Potentially interesting transformation  (Read 4521 times)

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Offline tmartin

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Potentially interesting transformation
« on: December 03, 2009, 02:51:05 PM »
So, following in Dan's shoes from last week, and as Heory had requested, here is my attempt at a somewhat interesting problem.  Hopefully it's not too easy or too challenging...


Edit: I realize the formula may be hard to see in my shrunk Chemdraw, it is: C26H31BrN2O5SSi.

Offline Heory

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Re: Potentially interesting transformation
« Reply #1 on: December 04, 2009, 01:33:34 AM »
 :)
« Last Edit: December 04, 2009, 01:45:16 AM by Heory »

Offline tmartin

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Re: Potentially interesting transformation
« Reply #2 on: December 04, 2009, 02:47:39 PM »
As a bonus: would anyone like to name the second compound on Heory's scheme?  I'll post the reference shortly, I'm just having some computer difficulties currently.

Offline movies

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Re: Potentially interesting transformation
« Reply #3 on: December 07, 2009, 12:45:08 PM »
Are you looking for endo-peroxide?

Offline tmartin

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Re: Potentially interesting transformation
« Reply #4 on: December 07, 2009, 01:35:05 PM »
It indeed was.  I actually completely forgot to post the link.  Thanks for the reminder  :)
ACIE 2004, 43, 2020-2023
DOI:   10.1002/anie.200453673

The paper is from 2004, a total synthesis of (-)-nakadomarin A.  I found this looking over some of my old class notes.  Interesting way to introduce the furan ring, I thought.  The endo peroxide is formed as a 1.2:1 mixture of diastereomers.  Both were taken on the the furan.

Offline Heory

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Re: Potentially interesting transformation
« Reply #5 on: December 07, 2009, 09:45:40 PM »
I thought you were looking for the compound's name. ;D

Offline tmartin

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Re: Potentially interesting transformation
« Reply #6 on: December 07, 2009, 11:34:02 PM »
Heh, sorry I should have been a little more clear.  I'll work on that for my next attempt at a "problem of the day/week"  ;D

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