Publication

Total Synthesis of (±)-Crokonoid A

2025

Abstract

We report herein a total synthesis of crokonoid A, featuring a dually bridged 6/7/6/5-fused tetracyclic carbon framework incorporating an unprecedented tricyclo[4.4.1.11,4]dodecane-2,11-dione core. The synthesis is highlighted by the following key transformations: (a) a regioselective decarboxylative allylation of a 1,3-dienyl carbonate to furnish an α-allyl-β,γ-unsaturated ketone; (b) a domino sequence involving ozonolysis, intramolecular aldol reaction, and acetalization to construct the bicyclo[4.3.1]decanedione core from a fused ring system, in which the acetalization step effectively stabilized the otherwise unstable aldol intermediate; (c) a palladium-catalyzed intramolecular cycloalkenylation of a ketone to assemble the bicyclo[3.2.1]octanedione system, in which the hybridization state of the neighboring carbon proved crucial for the success of this cyclization; and (d) SmI2–HMPA-mediated regio- and stereoselective reduction of the C14 ketone.

Official source

https://infoscience.epfl.ch/entities/publication/666f00c5-fe4e-4302-b985-9e30e1e4122d

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2025

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/666f00c5-fe4e-4302-b985-9e30e1e4122d

About this result

Related concepts (28)

Acetal

In organic chemistry, an acetal is a functional group with the connectivity . Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R' groups must be organic fragments not hydrogen. The two R' groups can be equivalent to each other (a "symmetric acetal") or not (a "mixed acetal"). Acetals are formed from and convertible to aldehydes or ketones and have the same oxidation state at the central carbon, but have substantially different chemical stability and reactivity as compared to the analogous carbonyl compounds.

Ketone

In organic chemistry, a ketone ˈkiːtoʊn is a functional group with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.

Total synthesis

Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest.

Related publications (1)

Total Synthesis of (±)-Crokonoid A

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Asymmetric Total Synthesis of Indole Alkaloids: (+)-Melonine, (-)-Ajmalicine, (+)-Mayumbine, (-)-Roxburghine C and Pd(II)-Catalyzed Wacker-Type Oxidation of Trisubstituted Alkenes