Literature DB >> 26315453

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

Praveen Kokkonda1, Keaon R Brown1, Trevor J Seguin2, Steven E Wheeler2, Shivaiah Vaddypally1, Michael J Zdilla1, Rodrigo B Andrade3.   

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.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  biomimetic synthesis; indole alkaloids; natural products; reaction mechanisms; total synthesis

Mesh：

Substances：

Year:  2015        PMID： 26315453      PMCID： PMC5012216          DOI： 10.1002/anie.201505198

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  16 in total

Review 1.  Simple indole alkaloids and those with a nonrearranged monoterpenoid unit.

Authors:  Minoru Ishikura; Koji Yamada; Takumi Abe
Journal:  Nat Prod Rep       Date:  2010-09-14       Impact factor: 13.423

2.  Synthesis of (±)-chamobtusin A by a presumed biomimetic aza-cyclization.

Authors:  Kazuma Kuzuya; Naoki Mori; Hidenori Watanabe
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

Review 3.  Simple indole alkaloids and those with a non-rearranged monoterpenoid unit.

Authors:  Masanori Somei; Fumio Yamada
Journal:  Nat Prod Rep       Date:  2005-01-10       Impact factor: 13.423

Review 4.  Simple indole alkaloids and those with a nonrearranged monoterpenoid unit.

Authors:  Minoru Ishikura; Koji Yamada
Journal:  Nat Prod Rep       Date:  2009-04-16       Impact factor: 13.423

5.  Indole and beta-carboline alkaloids from Geissospermum sericeum.

Authors:  Jonathan C P Steele; Nigel C Veitch; Geoffrey C Kite; Monique S J Simmonds; David C Warhurst
Journal:  J Nat Prod       Date:  2002-01       Impact factor: 4.050

6.  Total synthesis of (-)-leuconicine A and B.

Authors:  Gopal Sirasani; Rodrigo B Andrade
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

Review 7.  Simple indole alkaloids and those with a non-rearranged monoterpenoid unit.

Authors:  Minoru Ishikura; Takumi Abe; Tominari Choshi; Satoshi Hibino
Journal:  Nat Prod Rep       Date:  2013-05       Impact factor: 13.423

8.  Leucoridines A-D, cytotoxic Strychnos-Strychnos bisindole alkaloids from Leuconotis.

Authors:  Chew-Yan Gan; Tadahiro Etoh; Masahiko Hayashi; Kanki Komiyama; Toh-Seok Kam
Journal:  J Nat Prod       Date:  2010-06-25       Impact factor: 4.050

9.  Sequential one-pot cyclizations: concise access to the ABCE tetracyclic framework of strychnos alkaloids.

Authors:  Gopal Sirasani; Rodrigo B Andrade
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

10.  Synthesis and biological evaluation of pentacyclic strychnos alkaloids as selective modulators of the ABCC10 (MRP7) efflux pump.

Authors:  Christiana N Teijaro; Surendrachary Munagala; Senzhi Zhao; Gopal Sirasani; Praveen Kokkonda; Ekaterina V Malofeeva; Elizabeth Hopper-Borge; Rodrigo B Andrade
Journal:  J Med Chem       Date:  2014-12-08       Impact factor: 7.446
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  2 in total

1.  Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.

Authors:  Kristen M Flynn; In-Soo Myeong; Taylor Pinto; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2022-05-11       Impact factor: 16.383

2.  Biosynthesis of Grandione: An Example of Tandem Hetero Diels-Alder/Retro-Claisen Rearrangement Reaction?

Authors:  Ramiro F Quijano-Quiñones; Carolina S Castro-Segura; Gonzalo J Mena-Rejón; Mariana Quesadas-Rojas; David Cáceres-Castillo
Journal:  Molecules       Date:  2018-09-30       Impact factor: 4.411
  2 in total

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