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Topic: Retrosynthesis Problem  (Read 1930 times)

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Offline norml329

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Retrosynthesis Problem
« on: December 17, 2012, 05:14:56 PM »
I'm having a lot of trouble figuring out where to even begin with molecule. I know that I should probably start with a butene diol for the double bond on the left but from there I'm lost. Any help would be greatly appreciated as I've already tried looking up the molecule on reaxys, scifinder, and chemspider with no luck.

Offline discodermolide

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Re: Retrosynthesis Problem
« Reply #1 on: December 18, 2012, 12:18:22 AM »
This looks like a whole lot of stereoselective aldol chemistry. Or maybe even sugars as starting materials.
Perhaps Smith's dithiane chemistry.
A Suzuki coupling should make the tri-substituted C=C.
Try looking at these for possible starting points.

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Offline mevans86

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Re: Retrosynthesis Problem
« Reply #2 on: January 15, 2013, 07:53:01 PM »
Look for stereoselective crotylation or a vinylogous aldol reaction to install the homoallylic alcohol in the "northwest." Horner-Wadsworth-Emmons should be on your radar for the (E)-alkene in the "southwest." It's a big molecule, but break it down step by step and you'll get there!  :)

Offline NotExactly

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Re: Retrosynthesis Problem
« Reply #3 on: January 17, 2013, 02:52:08 PM »
Two words:  olefin metahesis.  Grubbs catalyst all day. 

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