Total Synthesis of Marine Sponge Bis(indole) Alkaloids of the Topsentin Class

2007 ◽  
Vol 72 (10) ◽  
pp. 3972-3975 ◽  
Author(s):  
Xavier Guinchard ◽  
Yannick Vallée ◽  
Jean-Noël Denis
Keyword(s):  
Total Synthesis ◽  
Marine Sponge ◽  
Indole Alkaloids

scholarly journals Total Synthesis of Marine Sponge Bis(indole) Alkaloids of the Topsentin Class.

ChemInform ◽  
2007 ◽  
Vol 38 (37) ◽  
Author(s):  
Xavier Guinchard ◽  
Yannick Vallee ◽  
Jean-Noel Denis
Keyword(s):  
Total Synthesis ◽  
Marine Sponge ◽  
Indole Alkaloids

Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity

2021 ◽  
Author(s):  
Robert M. Hohlman ◽  
David H. Sherman
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Indole Alkaloids ◽  
Recent Advances

This review covers isolation, biological activity, an overview of total synthesis efforts and recent biosynthetic discoveries related to hapalindole-type indole alkaloids.

scholarly journals The chemistry of mavacurane alkaloids: a rich source of bis-indole alkaloids

2021 ◽  
Author(s):  
Audrey Mauger ◽  
Maxime Jarret ◽  
Cyrille Kouklovsky ◽  
Erwan Poupon ◽  
Laurent Evanno ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Rich Source ◽  
Monoterpene Indole Alkaloids

This review presents the chemistry of mavacuranes, a subfamily of the monoterpene indole alkaloids, from their isolation, biosynthesis, total synthesis to their tendency to assemble with other partners to form intricate bis-indole alkaloids.

ChemInform Abstract: Total Synthesis of Agosterol A: An MDR-Modulator from a Marine Sponge.

ChemInform ◽  
2010 ◽  
Vol 33 (9) ◽  
pp. no-no
Author(s):  
Nobutoshi Murakami ◽  
Masanori Sugimoto ◽  
Mari Morita ◽  
Motomosa Kobayashi
Keyword(s):  
Total Synthesis ◽  
Marine Sponge

ChemInform Abstract: Total Synthesis of the Indole Alkaloids Henrycinol A (Ia) and B (Ib).

ChemInform ◽  
2014 ◽  
Vol 45 (51) ◽  
pp. no-no
Author(s):  
Kavirayani R. Prasad ◽  
John Eugene Nidhiry ◽  
Makuteswaran Sridharan
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids

scholarly journals Cytotoxic Sesterterpenes from Thai Marine Sponge Hyrtios erectus

Marine Drugs ◽  
2018 ◽  
Vol 16 (12) ◽  
pp. 474 ◽  
Author(s):  
Wirongrong Kaweetripob ◽  
Chulabhorn Mahidol ◽  
Pittaya Tuntiwachwuttikul ◽  
Somsak Ruchirawat ◽  
Hunsa Prawat
Keyword(s):  
Methyl Ether ◽  
Marine Sponge ◽  
Indole Alkaloids ◽  
Cytotoxic Activities ◽  
Spectroscopic Methods ◽  
The Absolute ◽  
Modified Mosher’S Method

Four sesterterpenes, erectusolides B, C, D, and seco-manoalide-25-methyl ether, two 2-furanone derivatives, erectusfuranones A and B, together with thirteen known sesterterpenes, (6Z)-neomanoalide-24-acetate, two diastereomers of 24-O-methylmanoalide, luffariolide B, manoalide, (6E)- and (6Z)-neomanoalide, seco-manoalide, scalarafuran, 12-acetylscalarolide, 12-epi-O-deacetyl-19-deoxyscalarin, 12-epi-scalarin, and 12-O-deacetyl-12-epi-scalarin, three indole alkaloids, 5-hydroxy-1H-indole-3-carbaldehyde, hyrtiosine A, and variabine B, and one norterpene, cavernosine were isolated from the marine sponge Hyrtios erectus. Their structures were determined by means of spectroscopic methods and the absolute configurations of the asymmetric centers were determined using the modified Mosher’s method. The cytotoxic activities for the isolated compounds have been reported.

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

scholarly journals Total Synthesis of (+)-Spiroindimicin A via Asymmetric Palladium-Catalyzed Spirocyclization

2021 ◽  
Author(s):  
Zhen Zhang ◽  
Sneha Ray ◽  
Leah Imlay ◽  
Lauren Callaghan ◽  
Hanspeter Niederstrasser ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Human Health ◽  
Neglected Tropical Diseases ◽  
Indole Alkaloids ◽  
Sleeping Sickness ◽  
Tropical Diseases ◽  
African Sleeping Sickness ◽  
Palladium Catalyzed ◽  
Natural Precursor

<p>The spiroindimicins are a unique class of chlorinated indole alkaloids characterized by three heteroaromatic rings structured around a congested spirocyclic stereocenter. Here, we report the first total synthesis of (+)-spiroindimicin A, which bears a challenging C-3’/C-5’’-linked spiroindolenine. We detail our initial efforts to effect a biomimetic oxidative spirocyclization from its proposed natural precursor, lynamicin D, and describe how these studies shaped our final abiotic 9-step solution to this complex alkaloid built around a key asymmetric Pd-catalyzed spirocyclization. Scalable access to spiroindimicins A, H, and their congeners has enabled discovery of their activity against several parasites relevant to human health, providing potential starting points for new therapeutics for the neglected tropical diseases leishmaniasis and African sleeping sickness.</p>

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