A modular synthesis of the lamellarins: total synthesis of lamellarin G trimethyl ether.
A modular synthesis of the lamellarin family of natural products has been developed that is based on the application of three iterative halogenation/cross-coupling reaction sequences. The ability to halogenate the pyrrole core in a regioselective fashion, even in the presence of highly electron-rich aryl substituents, has been established. The compatibility of Suzuki coupling conditions with free alcohols and phenols in the boronic acids has been employed to reduce the number of protection/deprotection steps. Indeed, the presence of a free phenol on boronic acid 3 has been determined to be critical for the successful final coupling in route to lamellarin G trimethyl ether, since protected versions fail to undergo coupling.
Handy
Scott T
ST
Department of Chemistry, State University of New York at Binghamton, Binghamton, New York 13902, USA. shandy@binghamton.edu
Zhang
Yanan
Y
Bregman
Howard
H
D001685:Biological Factors / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003374:Coumarins / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000138:chemical synthesis*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D001685:Biological Factors; D003374:Coumarins; D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D007546:Isoquinolines; C455554:lamellarin D; C486059:lamellarin G trimethyl ether