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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.50B [2011] >
IJC-B Vol.50B(04) [April 2011] >
| Title: | Toward a stereoselective synthesis of tetrahydroxy long chain base (LCB) and the synthesis of analogs of mannostatin A |
| Authors: | Raghavan, Sadagopan
Rathore, Kailash
Sridhar, B |
| Keywords: | Tetrahydroxy long chain base (LCB)
Mannostatin A
Sulfoxide
Sulfinylimine
Pummerer reaction |
| Issue Date: | Apr-2011 |
| Publisher: | NISCAIR-CSIR, India |
| 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. |
| Page(s): | 559-579 |
| CC License: |  CC Attribution-Noncommercial-No Derivative Works 2.5 India |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Source: | IJC-B Vol.50B(04) [April 2011]
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