In a convergent approach to the marine natural product (þ)-norrisolide (1) the two bicyclic ring systems are coupled through the C9 C10 bond to assemble the carbon framework in a late stage of the synthesis. Other highlights of the synthetic strategy include the formation of the unusual fused g-lactone–g-lactol motif of 1 through a sequence of oxidation reactions. T. P. Brady, S. H. Kim, K. Wen...

A chemical foundation for function-oriented studies of pectenotoxin 2 (PTX2) is described. A synthesis of the bicyclic GH-system, and the design and synthesis of a PTX2-analogue, is presented. While maintaining critical features for actin binding, and lacking the Achilles' heel for the natural product's anticancer activity (the AB-spiroketal), this first-generation analogue did not possess the ...

Cancer is a multifactorial disease that requires treatments able to target multiple intracellular components and signaling pathways. The natural compound, curcumin, was already described as a promising anticancer agent due to its multipotent properties and huge amount of molecular targets in vitro. Its translation to the clinic is, however, limited by its reduced solubility and bioavailability ...

The regulatory elements for nosiheptide biosynthesis were identified by a novel host-vector system with an endogenous gene within the biosynthetic gene cluster as a reporter gene. The present study offers a rapid and reliable method for the identification of regulatory elements in the biosynthesis of various bioactive natural products.

A route is described for the enantioselective synthesis of (R)-(-)-complanine, a marine natural product isolated from Eurythoe complanata, and known to be a causative agent in inflammation. An organocatalytic, asymmetric oxyamination of a homoconjugated all-Z-dienal intermediate provides versatile and efficient access to the natural product.

Internal bis-substituted propargylic diols were subjected to enzymatic kinetic resolution promoted by CAL-B. Employing a two round sequence EKR, mono- and bis-acetoxy propargylic products were obtained in a high enantiomeric ratio (E > 200). The efficiently resolved chiral 8b was applied in a concise synthesis of (S)-1b, an optically active natural product produced by fungi Clitocybe catinus.

Interest in multicomponent reactions (MCRs) has surged during the past two decades as interest in the efficient synthesis of small molecule libraries has gained prominence. MCRs fill an important niche in library synthesis by providing direct access to library compounds and by serving as starting points for Diversity-Oriented Synthesis (DOS). Recent advances in the area of MCR chemistry have in...

A modular synthetic approach was developed in which variation of the triplets of building blocks used enabled systematic variation of the macrocyclic scaffolds prepared. The approach was demonstrated in the synthesis of 17 diverse natural product-like macrocyclic scaffolds of varied (12-20-membered) ring size. The biological relevance of the chemical space explored was demonstrated through the ...

A sequential CH functionalization strategy for the synthesis of the marine alkaloid dictyodendrin B is reported. Our synthesis begins from commercially available 4-bromoindole and involves six direct functionalizations around the heteroarene core as part of a gram-scale strategy towards the natural product.

An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.