[jefferson987]

Hello all, I've been searching the net for days now looking for the steps to synthesize muscone. I haven't been able to find anything thats really helpful. Would anybody know of any good sources? Or even better, a proposed synthesis?

Here is the structure: http://upload.wikimedia.org/wikipedia/commons/5/5f/Muscone.png

[mickelcorleone]

ok you can use my word pad for this synthesis good luck




Download

Code: [Select]

http://rapidshare.com/files/333755519/Muscone.rtf

[sjb]

GIYF ? http://www.google.co.uk/search?q=muscone+synthesis ?

[jefferson987]

Thank you mickelcorleone for that file but there was no synthesis information in there so I'm not sure how thats supposed to help me

..And OF COURSE I googled, I found a bunch of very unspecific reaction mechanisms.. arrows that say "many steps".. things like that, but they dont say what the steps are.  I did manage to find this mechanism http://4.bp.blogspot.com/_NB5i1raeV2Y/Rxlo7wxVH3I/AAAAAAAAAR8/K4_624AJGtE/s1600-h/MUSCONE.GIF but it requires the use of grubs catalyst.. a very expensive reagent. Grubs catalyst was discovered fairly recently so there must be a way to synthesize muscone without it.

I'm just getting my feet wet with chemistry so any help would be appreciated.

[sjb]

There have been many efforts towards muscone over the years, but it's probable that the majority of older methods were concentrated on the racemate, which was then resolved at the end; whereas the more modern methods can induce the chirality earlier.

Going back in time even further, of course, most muscone was probably isolated via extraction from tissue or similar.

[uwichai]

You can take a look of this paper

Organic Letter 2009 vloume 11 No 2 pp 493-495. It give you the detail and discussion on prepare this compound stereoselctively. If you need the PDF file e-mail me at uwichai@hotmail.com and I will send it to you asap

goodluck

Uthai

[Med90]

the following paper has covered total synthesis of R and S muscone. I hope it will work for you.

http://www.jstage.jst.go.jp/article/bbb/66/6/66_1389/_article/-char/en

http://www.informaworld.com/smpp/content~db=all~content=a908617370?words=muscone

Good luck.