They Came From the Deep: Syntheses, Applications, and Biology of Ladderanes

Abstract

Ladderanes are hydrocarbons consisting of two or more fused cyclobutane rings. These molecules and their derivatives are of fundamental interest to physical organic chemists due to their strain and electronic properties. Recently, the astonishing discovery that some bacterial lipids contain ladderane substructures has revitalized interest in this class of molecules. This review describes the synthesis, reactivity, applications, and biology of ladderanes.

Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

“…2 Experimental and computational evidence suggests that ladderane lipids form a densely packed membrane around the anammoxosome and serve to limit the transmembrane diffusion of toxic or valuable metabolites from anammox catabolism. 3 Ladderane lipids likely impart a number of previously unobserved characteristics in membrane settings, but their biophysical characterization has been hampered by a lack of access to pure material. 3a An axenic culture of anammox bacteria is not available, and growth rates of enrichment cultures in laboratory reactors are slow (doubling times on the order of 1–2 weeks).…”

“…3 Ladderane lipids likely impart a number of previously unobserved characteristics in membrane settings, but their biophysical characterization has been hampered by a lack of access to pure material. 3a An axenic culture of anammox bacteria is not available, and growth rates of enrichment cultures in laboratory reactors are slow (doubling times on the order of 1–2 weeks). 4 Furthermore, anammox bacteria produce an array of ladderane and nonladderane lipids, which have proven inseparable on a preparative scale.…”

“…4 Furthermore, anammox bacteria produce an array of ladderane and nonladderane lipids, which have proven inseparable on a preparative scale. 3a To circumvent these difficulties, we designed a synthetic route that would allow us to access any ladderane lipid.…”

A G3(MP2B3) investigation on the structures and properties of silaprismanes

“…The structures of ladderanes are highly strained and these compounds have found important applications in materials science [2][3][4][5] and biology [2,6,7].…”

Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes

“…Due to the paucity of these molecules from biological sources, unconfirmed function, and interesting structure, which could inspire new strategies/methods, we sought to develop a synthesis of these molecules. 4 At the outset of our studies, only one enantioselective synthesis of [5]-ladderanoic acid (2) was known and was reported by Corey in 2006. 5 Therefore, we initially targeted the synthesis of [3]-ladderanol (1).…”