Topic: aza-steroid intermediate synthesis (Read 5306 times)

dielsalder · « **on:** April 10, 2009, 07:22:45 PM »

Hi guys i'm tying to make this synthesis (http://img7.imageshack.us/img7/2493/ghfghf.jpg) but i can't figure it out how to make the second step . i have made the first step with a Robinson annulation

someone have an idea ?

lutesium · « **Reply #1 on:** April 11, 2009, 07:34:39 AM »

What do you want as the final product? Is that:
(7aR)-1-(1-hydroxy-1-(3-isopropyl-5-methylene-2,5-dihydro-1H-pyrrol-2-yl)propan-2-yl)-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one

dielsalder · « **Reply #2 on:** April 11, 2009, 01:57:00 PM »

5-(1-hydroxy-2-((7aR)-7a-methyl-5-oxo-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)propyl)-4-isopropyl-1H-pyrrol-2(5H)-one

I forgot an Oxygen on the double bond

I need a synthetic strategy to add the 4-isopropyl-1-methyl-1H-pyrrol-2(5H)-one group on the rest of the molecule

lutesium · « **Reply #3 on:** April 12, 2009, 07:08:56 AM »

May he be 4-isopropyl-1H-pyrrol-2(5H)-one because if he is 4-isopropyl-1-methyl-1H-pyrrol-2(5H)-one you'll need a DeMethylation of the Nitrogen maybe through Von Braun Reaction to reach the desired molecule.

Lutesium...

dielsalder · « **Reply #4 on:** April 12, 2009, 01:37:39 PM »

thx Lutesium

but i have made some mistake in my sketch im sorry ... lets start over

i need a synthesis strategy to get the final product with minimun step

Dolphinsiu · « **Reply #5 on:** April 12, 2009, 02:45:18 PM »

I don't know if the strange synthesis in attached file is useful since I try to draw in ChemSketch copied and pasted in Word file.

dielsalder · « **Reply #6 on:** April 12, 2009, 03:19:47 PM »

thanks man i never thaught about BH3 witch give anti-markovnikov product

i'm not clearly understand the second step with NaOH

Dolphinsiu · « **Reply #7 on:** April 13, 2009, 03:30:26 AM »

Yes. second step is very strange. actually I want to use Konvegxxx reaction (I have forgot the name), but it seems very strange. I also hope anyone having much organic synthetic knowledge can help you.

Dolphinsiu · « **Reply #8 on:** April 13, 2009, 04:55:32 AM »

Maybe..we can use McMurry reaction in second step....I don't know if alpha beta ketone group would reacts...actually, I also have throught about Grignard reagent...but the OH group is in opposite side...so really need to think about anti-Markovnikov or carbocation rearrangement...

Actually I also have thought Wittig reaction for second step. Again, I don't know if alpha beta ketone group would be affected.

dielsalder · « **Reply #9 on:** April 13, 2009, 06:51:04 PM »

thx Dolphinsiu

you're right i can use the mc murry or wittig ... and i thing i can protect my a,b-ketone with tioacetals

Topic: aza-steroid intermediate synthesis (Read 5306 times)

dielsalder

aza-steroid intermediate synthesis

lutesium

Re: aza-steroid intermediate synthesis

dielsalder

Re: aza-steroid intermediate synthesis

lutesium

Re: aza-steroid intermediate synthesis

dielsalder

Re: aza-steroid intermediate synthesis

Dolphinsiu

Re: aza-steroid intermediate synthesis

dielsalder

Re: aza-steroid intermediate synthesis

Dolphinsiu

Re: aza-steroid intermediate synthesis

Dolphinsiu

Re: aza-steroid intermediate synthesis

dielsalder

Re: aza-steroid intermediate synthesis

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