Total synthesis of (-)-himgaline

ORGN 377

Unmesh Shah, unmesh.shah@spcorp.com1, Samuel Chackalamannil1, A. K. Ganguly, akganguly1@aol.com2, Mariappan V. Chelliah, mariappan.chelliah@spcorp.com1, Sergei Kolotuchin1, Alexei Buevich1, and Andrew T. McPhail3. (1) Chemical Research, Schering-Plough Research Institute, Kenilworth, NJ 07033, (2) Department of Chemistry, Stevens Institute of Technology, Castle Point on Hudson, Hoboken, NJ 07030, (3) Department of Chemistry, Duke University, P. M. Gross Chemistry Laboratory, Durham, NC 27708
The rare rain forest tree Galbulimima belgraveana, found in Northern Australia and Papua New Guinea, has been the source of several complex alkaloids. Among these, himbacine (1) has attracted considerable synthetic attention due to its promising pharmacological properties. Consequently, several total syntheses have been recently completed. Himgaline (2) and GB 13 (3) are among the congeners of himbacine with even more pronounced structural complexity. Convergent, enantioselective total synthesis of these alkaloids was carried out starting from (S)-3-butyn-2-ol using a highly diastereoselective intramolecular Diels-Alder reaction and an aza-Michael facilitated decarboxylation reaction as key steps.

 

Total Synthesis of Complex Molecules
1:00 PM-4:20 PM, Tuesday, March 27, 2007 McCormick Place East -- Room E352, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007