2016
DOI: 10.1021/acs.accounts.5b00493
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Diverse Natural Products from Dichlorocyclobutanones: An Evolutionary Tale

Abstract: 11-Nor PGE2 was prepared in our laboratory several years ago and used to obtain the corresponding ring-expanded γ-butyrolactam, γ-butyrolactone, and cyclopentanone derivatives. The conversion of a cyclobutanone into a cyclopentanone had relatively little precedent and merited further study. It was soon found that the presence of a single chlorine adjacent to the carbonyl not only greatly accelerated the reaction with ethereal diazomethane, but also substantially enhanced its regioselectivity; not surprisingly,… Show more

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Cited by 37 publications
(19 citation statements)
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“…Many natural products include a γ‐butyrolactone or γ‐butyrolactam moiety as structural element [1,2] . Especially the γ‐butyrolactone motif is present in about 10 % of all natural products [3–5] .…”
Section: Introductionmentioning
confidence: 99%
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“…Many natural products include a γ‐butyrolactone or γ‐butyrolactam moiety as structural element [1,2] . Especially the γ‐butyrolactone motif is present in about 10 % of all natural products [3–5] .…”
Section: Introductionmentioning
confidence: 99%
“…Especially the γ‐butyrolactone motif is present in about 10 % of all natural products [3–5] . In total syntheses, a common strategy to synthesize the γ‐butyrolactone motif is the Baeyer‐Villinger oxidation [2,6] . Herein, an ester is formed from a ketone by using peroxyacids or peroxides.…”
Section: Introductionmentioning
confidence: 99%
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