1016650-10-4Relevant articles and documents
Modular total syntheses of lamellarin G trimethyl ether and lamellarin S
Hasse, Katrin,Willis, Anthony C.,Banwell, Martin G.
experimental part, p. 88 - 99 (2011/03/21)
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). The first total synthesis of the marine alkaloid lamellarin S is described.
Design and synthesis of lamellarin D analogues targeting topoisomerase I
Ohta, Takeshi,Fukuda, Tsutomu,Ishibashi, Fumito,Iwao, Masatomo
experimental part, p. 8143 - 8153 (2010/02/17)
(Chemical Equation Presented) A general synthetic route to rationally designed lamellarinDanalogues, 1-dearyllamellarinD(1) and 1-substituted 1-dearyllamellarin D (2), has been developed. The key pentacyclic intermediate 22 was prepared by palladium-catalyzed direct arylation of 12, which in turn was synthesized via C-2-selective lithiation of 15 followed by palladium-catalyzed cross-coupling as the key reactions. Compound 22 was converted to a wide range of C-1-substituted analogues 2 via regioselective electrophilic substitution and palladium-catalyzed cross-coupling reactions.
Di- and triarylsubstituted pyrroles by sequential regioselective cross-coupling reactions
Schroeter, Sven,Bach, Thorsten
, p. 569 - 594 (2008/09/18)
The di- and tribrominated pyrroles, such as methyl 3,4,5-tribromo- pyrrole-2-carboxylate (1), ethyl 3,4,5-tribromopyrrole-2-carboxylate (2), methyl 4,5-dibromopyrrole-2-carboxylate (3), and 4,5-dibromo-2-nitropyrrole (4), were prepared and evaluated for t
