Total Synthesis of (-)-Pateamine A, a Novel Immunosuppressive Agent from Mycale sp.

ChemInform ◽  
2004 ◽  
Vol 35 (34) ◽  
Author(s):  
Gerald Pattenden ◽  
Douglas J. Critcher ◽  
Modesto Remuinan
2004 ◽  
Vol 82 (2) ◽  
pp. 353-365 ◽  
Author(s):  
Gerald Pattenden ◽  
Douglas J Critcher ◽  
Modesto Remuiñán

A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A (1) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp2–sp2 coupling reaction to elaborate the E,Z-diene macrolide core 23 and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.Key words: pateamine A, immunosuppressive agent from marine sponge Mycale sp, total synthesis, novel 19-membered bis-lactone, thiazole metabolite, polyenamine, Stille reaction, sulfinimines, chiral β-amino esters.


2005 ◽  
Vol 7 (17) ◽  
pp. 3745-3748 ◽  
Author(s):  
Kazuhiro Watanabe ◽  
Katsuhiko Iwasaki ◽  
Toshiaki Abe ◽  
Munenori Inoue ◽  
Kôichi Ohkubo ◽  
...  

ChemInform ◽  
2006 ◽  
Vol 37 (1) ◽  
Author(s):  
Kazuhiro Watanabe ◽  
Katsuhiko Iwasaki ◽  
Toshiaki Abe ◽  
Munenori Inoue ◽  
Koichi Ohkubo ◽  
...  

ChemInform ◽  
2010 ◽  
Vol 25 (15) ◽  
pp. no-no
Author(s):  
J. B. NERENBERG ◽  
D. T. HUNG ◽  
P. K. SOMERS ◽  
S. L. SCHREIBER

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