Formation of tricyclo[6.3.0.02,5]undecane derivatives during attempts to make the rumphellatin A–C oxacarbon skeleton

1-Sulfonylcyclopropanols are employed here as efficient cyclopropanone equivalents in a formal vinylidene insertion process, providing the first general synthetic route to enantioenriched alkylidenecyclobutanones. The addition of an alkenyl-Grignard reagent leads to an alkenylcyclopropanol capable of electrophilic activation by N-bromosuccinimide, triggering a regio-and stereospecific 1,2-migration and affording alkylidenecyclobutanones after elimination. Activation of the intermediate with other electrophiles such as HCl or mCPBA leads to the formation of various chiral cyclobutanones and γ-lactones via alternative pathways.

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Stereospecific Synthesis of Enantioenriched Alkylidenecyclobutanones via Formal Vinylidene Insertion into Cyclopropanone Equivalents

Poteat

Lindsay

2021

Org. Lett.

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Bioinspired Semisynthesis and Structure Revisions of Chlorinated Norsesquiterpenoids Rumphellatins A–C

Stakanovs,

Blazevica,

Rasina

et al. 2024

Org. Lett.

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The first synthesis of chlorine-containing hemiketals, rumphellatins A−C (1−3), previously inaccessible by means of total synthesis, was achieved starting from commercially available (−)-β-caryophyllene oxide (7). Structures of rumphellatins A (1) and C (3) were revised, while structures of rumphellatin B (2) and intermediate rumphellolide C ( 19) were confirmed. The study expands availability of exotic norsesquiterpenoids for profiling their biological activity as well as facilitates the elucidation of biosynthetic pathways of their formation.

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Formation of tricyclo[6.3.0.02,5]undecane derivatives during attempts to make the rumphellatin A–C oxacarbon skeleton

Cited by 2 publications

References 56 publications

Stereospecific Synthesis of Enantioenriched Alkylidenecyclobutanones via Formal Vinylidene Insertion into Cyclopropanone Equivalents

Stereospecific Synthesis of Enantioenriched Alkylidenecyclobutanones via Formal Vinylidene Insertion into Cyclopropanone Equivalents

Bioinspired Semisynthesis and Structure Revisions of Chlorinated Norsesquiterpenoids Rumphellatins A–C

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