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|Title:||Toward a stereoselective synthesis of tetrahydroxy long chain base (LCB) and the synthesis of analogs of mannostatin A|
|Keywords:||Tetrahydroxy long chain base (LCB);Mannostatin A;Sulfoxide;Sulfinylimine;Pummerer reaction|
|Abstract:||Efforts toward the stereoselective synthesis of tetrahydroxy long chain base and analogs of mannostatin A are described. The sulfinyl moiety has been efficiently utilized as an intramolecular nucleophile for oxidative functionalization of an alkene and regioselective opening of an epoxide. Nucleophilic addition to sulfinylimine has been used for the introduction of amino stereogenic center. Pummerer reaction has not been successful with a free N-H group at -carbon. Pummerer reaction on a N,O-acetonide furnishes an aldehyde. Attempted Wittig olefination to access the protected derivative of long chain base have failed. The analog of mannostatin could not be prepared by intramolecular addition of a sulfinyl carbanion to an imine but could be prepared by radical chemistry.|
|Appears in Collections:||IJC-B Vol.50B(04) [April 2011]|
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