Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 1, Pages 88-99Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001133
Keywords
Natural products; Alkaloids; Pyrroles; Cross-coupling
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Funding
- Gottlieb Daimler and Karl Benz Foundation
- Australian Research Council [DP0771749]
- Australian Research Council [DP0771749] Funding Source: Australian Research Council
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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).
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