Concise Synthesis of the C15–C38 Fragment of Okadaic Acid: Application of the Suzuki–Miyaura Reaction to Spiroacetal Synthesis

Abstract

A concise synthetic entry to the C15-C38 fragment of okadaic acid by exploiting a Suzuki-Miyaura reaction for the rapid assembly of the spiroacetal substructures has been developed. The present synthesis was completed in 19 linear steps from a commercially available material, showcasing the efficiency of our synthetic strategy.

C-glycosides analogues of the okadaic acid central fragment exert neuroprotection via restoration of PP2A-phosphatase activity: A rational design of potential drugs for Alzheimer's disease targeting tauopathies

“…The drugability of designed compounds was maintained according to physicochemical properties related to Lipinski's rule of five (Table S1, supplementary material). To furnish the desired entities, we have taken advantage of the Organic Chemistry literature centered on pursuing the total synthesis of OA [61][62][63] and other dinophysistoxins [64], where the contributions of Forsyth's group have been crucial.…”

Chemical Syntheses and Chemical Biology of Carboxyl Polyether Ionophores: Recent Highlights

“…We have tried to extract the strategic disconnections toward the carbon skeletons and key methods involved in the construction of the structural subunits, rather than comprehensively detailing every synthetic step from all the different approaches. A compilation of synthetic studies on other carboxyl polyether ionophore natural products completed in the time period from 2001 to 2018 is given in Table S1 (Supporting Information) with key transformations highlighted …”

Tandem Achmatowicz Rearrangement and Acetalization of 1-[5-(Hydroxyalkyl)-furan-2-yl]-cyclobutanols Leading to Dispiroacetals and Subsequent Ring-Expansion to Form 6,7-Dihydrobenzofuran-4(5H)-ones

“…Dispiroheterocycles are present in a variety of natural products, pharmaceuticals, and other biologically active molecules, − and the development of efficient methods for their construction is therefore of interest to researchers in the fields of organic synthesis and medicinal chemistry. − Spiroacetals are of particular interest because they are found in numerous biologically active natural products isolated from plants, fungi, and marine organisms. − In addition, the spiroacetal moiety contributes to the bioactivities of insect sex pheromones, polyketide antibiotics, and microtubule stabilizing agents, and it represents a privileged scaffold in drug discovery research. − Accordingly, the synthesis of structurally novel dispiroacetals and developing efficient methods for them are highly desirable.…”