Recent Progress in the Synthesis of Sesquiterpenoid Involving Spirocyclic Carbon Framework

Abstract

Spirocarbocyclic natural products have been attracting considerable attention from synthetic organic chemists. This review focused on total syntheses of sesquiterpenoids involving spiro[4.5]decane and spiro[5.5]undecane scaffolds, compiling syntheses of colletoic acid, cubebol, axenol, vetispirene, hinesol, agarospirol, axenol, gleenol, exiguamide, exigurin, erythrodiene, spirojatamol, antroalbocin A, omphalic acid, dactylone, and aplydactonee since 2015.

Copper-Catalyzed Enantioselective Synthesis of Spirohydroindoles by Ethoxyformylmethylene Oxindole and Iminoester 1,3-Dipole Cycloaddition: An Examination of Associated Biological Activities

“…Spirocyclic skeletal structures involving intricate formations and well-defined stereoconformations are abundant in natural products and synthetic drugs . The spiro­[pyrrolidin-3,3′-oxindole] is a prime example of a chiral spirocyclic fragment, with an associated stereoisomerism and chemical reactivity that has been the subject of significant research in medicinal chemistry.…”

“…Spirocyclic skeletal structures involving intricate formations and well-defined stereoconformations are abundant in natural products and synthetic drugs. 1 The spiro[pyrrolidin-3,3′-oxindole] is a prime example of a chiral spirocyclic fragment, 2 with an associated stereoisomerism and chemical reactivity that has been the subject of significant research in medicinal chemistry. Spirotryprostatins A, pteropodine, cyanogramide, MI-219, rhynchophylline, and strychnofoline ( Figure 1 ) have exhibited excellent antitumor, antibacterial, and other biological activities.…”