Biomimetic Total Syntheses of (-)-Leucoridines A and C through the Dimerization of (-)-Dihydrovalparicine.

Authors :: Kokkonda P
Brown KR
Seguin TJ
Wheeler SE
Vaddypally S
Zdilla MJ
Andrade RB
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2015 Oct 19; Vol. 54 (43), pp. 12632-5. Date of Electronic Publication: 2015 Aug 28.
Publication Year :: 2015
Abstract: Concise biomimetic syntheses of the Strychnos-Strychnos-type bis-indole alkaloids (-)-leucoridine A (1) and C (2) were accomplished through the biomimetic dimerization of (-)-dihydrovalparicine (3). En route to 3, the known alkaloids (+)-geissoschizoline (8) and (-)-dehydrogeissoschizoline (10) were also prepared. DFT calculations were employed to elucidate the mechanism, which favors a stepwise aza-Michael/spirocyclization sequence over the alternate hetero-Diels-Alder cycloaddition reaction.<br /> (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Subjects :: Biomimetics methods
Cycloaddition Reaction methods
Dimerization
Indole Alkaloids chemistry
Magnoliopsida chemistry
Models, Molecular
Stereoisomerism
Indole Alkaloids chemical synthesis

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