Short and flexible route to 3,4-diarylpyrrole marine alkaloids: syntheses of permethyl storniamide A, ningalin B, and lamellarin G trimethyl ether

A highly efficient route to 3,4-diarylpyrrole marine alkaloids has been developed using Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki cross-coupling of the 3,4-dihydroxypyrrole bis-triflate derivatives as key reactions. Based on this approach, formal syntheses of permethyl storniami...

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Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 24; pp. 4443 - 4446
Main Authors Iwao, Masatomo, Takeuchi, Toshiro, Fujikawa, Naotaka, Fukuda, Tsutomu, Ishibashi, Fumito
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.06.2003
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALPHA 20-SULFATE
BIOMIMETIC TOTAL-SYNTHESIS
POLYCITONE
1ST SYNTHESIS
COUPLING REACTION
EFFICIENT SYNTHESIS
LUKIANOL
PYRROLES
CONCISE SYNTHESIS
DERIVATIVES
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Summary:A highly efficient route to 3,4-diarylpyrrole marine alkaloids has been developed using Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki cross-coupling of the 3,4-dihydroxypyrrole bis-triflate derivatives as key reactions. Based on this approach, formal syntheses of permethyl storniamide A and ningalin B, and a total synthesis of lamellarin G trimethyl ether have been achieved. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)01031-1