[Seanlet]

Hi,
   I was asked, for a bet (1 beer) if I could find a synthetic route to the title compound (SMILES O=C1[C@@H](C)CN(CC2=CC=CO2)CC1). My solution involved the synthesis of methyl 3-((furan-2-ylmethyl)(3-methoxy-3-oxopropyl)amino)-2-methylpropanoate (SMILES CC(CN(CC1=CC=CO1)CCC(OC)=O)C(OC)=O) from furan-2-ylmethanamine (SMILES NCC1=CC=CO1) which in turn come from methyl 4-oxobutanoate & methyl 3-chloro-2-methylpropanoate.

My question is, will chiral methyl 3-chloro-2-methylpropanoate yield the chiral N-furan-2-ylmethyl-3-methyl-4-propanone?

Reaxys doesn't mention anything similar, my search of ACS & Wiley sheds no light on it and after struggling for 6 weeks; I look to be losing a pint over this?

Can anyone point me to a paper where the mechanistics of the condensation are dealt with?


Many thanks to anyone who can shed SOME light on this...

[Seanlet]

imageupload.org/?d=566225611    <----cannot get it to display, but it's here!


That is the target compound and I need to be able to be able to provide a route that is capable of doing both isomers.

The ring-formation idea is derived from:

Carabateas; Grumbach
Journal of Medicinal and Pharmaceutical Chemistry, 1962, volume 5, pages 913,916

But obviously replacing the benzylamine with furan-2-ylamine.

The simple question is, can the methyl 2-methyl-3-butenoate (CAS 51747-33-2) be obtained optically pure? I find a single reference:

Okrasa, Krzysztof; Wilding, Matthew; Goodall, Mark; Micklefield, Jason; Levy, Colin; Leys, David; Baudendistel, Nina; Hauer, Bernhard
Angewandte Chemie, International Edition, 2009, volume 48, #41 pages 7691-7694


But I'm not sure if this reference is to be trusted.



I would be SO grateful if someone could give me a pointer or two...

[discodermolide]

Here may be one possibility.
All materials are commercially available. The Boc alpha methyl compound is available as a racemate, a resolution should be possible. Otherwise i suggest a chiral alkylation.

[Seanlet]

imageupload.org/?d=566225611    <----cannot get it to display, but it's here!

Does Megaupload still exist? I thought Kim DotCom had the rug pulled from under him?

Any other link?

Many thanks for all of the responses - there are some really great people here!