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Modular Total Syntheses of Lamellarin G Trimethyl Ether and Lamellarin S
Author(s) -
Hasse Katrin,
Willis Anthony C.,
Banwell Martin G.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001133
Subject(s) - chemistry , moiety , halogenation , heck reaction , pyrrole , alkylation , total synthesis , ether , stereochemistry , organic chemistry , palladium , catalysis
Modular total syntheses of the title compounds 2 and 3 are reported. The key pyrrolic building block 8 was prepared from the readily accessible pyrrole 6 via a di‐iodination/mono‐deiodination sequence. Suzuki–Miyaura cross‐coupling of compound 8 with boronate ester 9 afforded lactone 10 . Bromination of compound 10 followed by N ‐alkylation under Mitsunobu conditions afforded the fully substituted pyrrole 13 that engaged in a second Suzuki–Miyaura cross‐coupling reaction with boronic acid 14 to give compound 15 . Hydrolysis of the ester moiety within the last compound afforded acid 16 that engaged in a decarboxylative Heck cyclization process to give lamellarin G trimethyl ether ( 3 ). A related sequence of reactions starting from building block 8 and using the isopropoxy‐substituted arenes 22 , 25 and 27 has allowed for the completion of the first total synthesis of lamellarin S ( 2 ).