Journal
TETRAHEDRON
Volume 66, Issue 33, Pages 6514-6525Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.05.048
Keywords
Palladium catalysis; Total synthesis; Alkaloid; Mechanism; Cascade reaction
Categories
Funding
- NIGMS NIH HHS [R01 GM030859-17, R01 GM030859-27, R01 GM030859-20, R01 GM030859, R01 GM030859-18, R01 GM030859-21, R01 GM030859-28, R01 GM030859-22, R01 GM030859-19] Funding Source: Medline
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A catalytic intramolecular Heck reaction, followed by capture of the resulting eta(3)-allylpalladium intermediate by a tethered diketopiperazine, is the central step in a concise synthetic route to (-)-spirotryprostatin B and three stereoisomers. This study demonstrates that an acyclic, chiral eta(3)-allylpalladium fragment generated in a catalytic asymmetric Heck cyclization can be trapped by even a weakly nucleophilic diketopiperazine more rapidly than it undergoes diastereomeric equilibration. (C) 2010 Elsevier Ltd. All rights reserved.
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