ABSTRACT
Marine microorganisms are an important source of natural polyketides, which have become a significant reservoir of lead structures for drug design due to their diverse biological activities. In this review, we provide a summary of the resources, structures, biological activities, and proposed biosynthetic pathways of the benzyl alcohol/salicylaldehyde-type polyketides. In addition, the total syntheses of these secondary metabolites from their discoveries to the present day are presented. This review could be helpful for researchers in the total synthesis of complex natural products and the use of polyketide bioactive molecules for pharmacological purposes and applications in medicinal chemistry.
Subject(s)
Biological Products , Polyketides , Polyketides/chemistry , Polyketide Synthases/metabolism , Fungi/metabolism , Biological Products/chemistry , Benzyl AlcoholsABSTRACT
The paper describes the first total synthesis of natural varioxiranol A by chiral pool approach and confirmation of its absolute configuration by single-crystal X-ray analysis. The target varioxiranol A and its 4-epimer were obtained after 10 steps from single and available chiral source 1,2-O-isopropylidene-d-glyceraldehyde in an overall yield of 10% and 6%, respectively. A synthetic strategy based on the Juliaâ»Kocienski coupling reaction between aromatic sulfone and corresponding aldose derivative makes it possible to prepare other interesting polyketide derivatives (varioxiranols B-G, varioxirane, varioxiranediols).
Subject(s)
Polyketides/chemistry , Polyketides/chemical synthesis , Crystallography, X-Ray , Molecular Structure , StereoisomerismABSTRACT
The constitution and relative configuration at the stereogenic centres and stereochemistry of the C-C double bond formed during Pd(II)-catalysed domino reaction was established by X-ray analysis of the title compound, C(10)H(14)O(4). The asymmetric unit contains two mol-ecules.