Absolute configurations of cytotoxic marine cembranolides; Consideration of mosher's method
TL;DR: In this paper, the stereochemistry of the cembranolides isolated from the soft coral Sinularia mayi has been elucidated by means of 2D NMR spectroscopy and X-ray crystallography.
About: This article is published in Tetrahedron Letters.The article was published on 1988-01-01. It has received 123 citations till now.
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TL;DR: This review covers the literature published in 2014 for marine natural products, with 1116 citations referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms.
4,649 citations
TL;DR: An antioxidant mechanism of curcumin in polyunsaturated lipids was proposed, which consisted of an oxidative coupling reaction at the 3'-position of theCurcumin with the lipid and a subsequent intramolecular Diels--Alder reaction.
Abstract: As a part of a research project on the antioxidant mechanism of natural phenolics in food components, curcumin, a turmeric antioxidant, was investigated in the presence of ethyl linoleate as one of the polyunsaturated lipids. During the antioxidation process, curcumin reacted with four types of linoleate peroxyl radicals. Six reaction products were observed in the reaction and subsequently isolated. Their structures were determined by physical techniques, revealing that they have novel tricyclic structures, including a peroxyl linkage. On the basis of the formation pathway for their chemical structures, an antioxidant mechanism of curcumin in polyunsaturated lipids was proposed, which consisted of an oxidative coupling reaction at the 3'-position of the curcumin with the lipid and a subsequent intramolecular Diels--Alder reaction.
225 citations
TL;DR: In this article, a macrolactonization approach was used to synthesize epothilones with high convergency and flexibility, and the synthesis of microtubule binding antitumor agents was described.
Abstract: The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9−12 and 15 were constructed by asymmetric processes and coupled via Wittig, aldol, and macrolactonization reactions to afford the basic skeleton of epothilones and that of several of their analogues by a relatively short route. The utilization of intermediate 14, obtained via a stereoselective Wittig reaction and its Enders coupling to SAMP hydrazone 13 (Scheme 8), in combination with a stereoselective aldol reaction with the modified substrate 69 (Scheme 10) improved the stereoselectivity and efficiency of the total synthesis of these new and highly potent microtubule binding antitumor agents.
216 citations
TL;DR: In this article, the absolute configurations of marine diterpenes, 7 and 8, were elucidated by means of Mosher's method using 1H NMR spectroscopy at 500 MHz.
156 citations
TL;DR: The sorbicillinoids are a family of hexaketide metabolites that have been isolated from a variety of fungal sources, collected from both marine and terrestrial sources and has led to controversy surrounding the biosynthetic pathway responsible for the natural production of these compounds.
124 citations
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TL;DR: Denticulatolide, an ichthyotoxic cembranoid diterpene bearing acetoxy, α-methylene γ-lactone, and cyclic peroxide functions, has been isolated from the soft coral Lobophytum denticulatum as discussed by the authors.
44 citations
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