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.

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 Julia–Kocieński coupling reaction between aromatic sulfone and corresponding aldose derivative makes it possible to prepare other interesting polyketide derivatives (varioxiranols B-G, varioxirane, varioxiranediols).

The synthesis of 4-(1H-tetrazol-5-yl)-2-(p-tolyl)quinoline 4 as a possible modification of the biphenyltetrazole substructure of losartan 1 is described. The transformation of 2-(p-tolyl)quinoline-4-carbonitrile 3 to the corresponding tetrazole 4 was carried out by the reaction of trimethysilyl azide and dibutyltin oxide as a catalyst in refluxing toluene. The title compound (4) was characterized by IR, ¹H NMR, ¹³C NMR, and HRMS.