Synthesis of pretubulysin-derivatives via the TubUgi-approach.
The Ugi reaction is found to be a very powerful tool for the synthesis of (pre)tubulysin derivatives, allowing the introduction of various functionalized side chains in only one step. While polar groups such as amides are not well tolerated, unpolar side chains such as allyl or propargyl ether are well accepted. These functionalities also allow subsequent modifications in the side chain, e.g. via ring closing metathesis or Click reaction.
Institute of Organic Chemistry, Saarland University, P.O. Box 151150, 66041 Saarbrücken, Germany. u.kazmaier@mx.uni-saarland.de.
Judith
J
Hoffmann
Jan
J
Gorges
Lukas
L
Junk
Uli
U
Kazmaier
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D057930:Click Chemistry; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry; D009231:Myxococcales / Q000737:chemistry*; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D004987:Ethers; D009842:Oligopeptides; C531209:propargyl ether; C575012:pretubulysin