Agelastatin a, a new skeleton cytotoxic alkaloid of the oroidin family. Isolation from the axinellid sponge Agelas dendromorpha of the coral sea

Abstract

Agelastatin A, isolated from the axinellid sponge Agelas dendromorpha of the Coral Sea, is a new-skeleton alkaloid with, unusually for the oroidin family to which it belongs, marked cytotoxicity toward tumour cells in culture.

Recent advances in the total synthesis of agelastatins

“…Pietra proposed a cascade route starting from a hymenidin-like precursor 10 (Scheme 1A) [5]; while Mourabit prefers to begin with an oxidized hymenidine precursor (12) that can proceed through a cyclization to install the C-ring, which can undergo pyrrole-participated conjugated addition to provide the tetracycle skeleton (Scheme 1B) [14]. Note that Mourabit's proposal relies on multiple imine-enamine tautomerizations.…”

“…Agelastatin A (1) was originally isolated by Pietra et al in 1993 from the axinellid sponge Agelas dendromorpha collected in the Coral Sea near New Caledonia [5] (Fig. 1).…”

Synthesis of Oxazolidin‐2‐ones and Imidazolidin‐2‐ones Directly from 1,3‐Diols or 3‐Amino Alcohols using Iodobenzene Dichloride and Sodium Azide

“…Oxazolidin-2-one and imidazolidin-2-one motifs are common structural units in many natural products, [1] pharmaceuticals, [2] and biologically active compounds, [3] as exemplified by (À)-agelastatin A, [1a] linezolid, [2b] and KVI-020 [3a] ( Figure 1). Oxazolidin-2-ones and imidazolidin-2-ones can also serve as chiral auxiliaries in a number of asymmetric reactions; [4] in particular, Evans auxiliaries, bearing oxazolidin-2-one moiety, are extensively applied in asymmetric alkylation, [5] aldol reaction, [6] Diels-Alder reaction, [7] and asymmetric fluorination reaction.…”

Bromopyrrole Alkaloids from Okinawan Marine Sponges <i>Agelas</i> spp.

“…15) As part of that research project, bromopyrrole alkaloids in sponges Agelas spp. (SS-162, SS-307) were investigated, resulting in the isolation of 18 unique alkaloids including five dimeric bromopyrrole alkaloids (1-5), ten monomeric bromopyrrole alkaloids (6)(7)(8)(9)(10)(11)(12)(13)(14)(15), and three conjugates of monomeric bromopyrrole alkaloid and hydroxykynurenine (16)(17)(18). In this mini-review, we describe the isolation, structure elucidation, and antimicrobial activities of these alkaloids.…”