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• W3208085129 abstract "Abstract A Wittig reaction of 3‐hydroxyphtalide ( 11 ) gave ortho ‐styrene‐2‐carboxylic acid ( 12 ). Its Weinreb amide 13 acylated heterosubstituted methyllithiums. This led to aryl “methyl” ketones whose sp 3 ‐carbon was substituted by Cl+OMe (in 14 a ), 2×Cl (in 14 b ), OtBu (in 17 a ), SPh (in 17 b ) or SO 2 Ph (in 17 c ). The enolates of these ketones were C‐allylated. This furnished the benzene‐fused nona‐1,8‐dienones 7 a – b and 9 a – c , respectively. Ring‐closing metatheses provided the corresponding benzocycloheptadienones 8 a ‐ b and 10 a – c . Their ketone moieties were α,α‐disubstituted (in 8 a – b ) or α‐monosubstituted (in 10 a – c ). Each substitution pattern allowed to generate the hydroxyenone motif of the corresponding benzocycloheptatrienone—or 6,7‐benzotropolone— 6 a : The MeO‐ and PhS‐containing benzocycloheptadienone 8 a gave 6,7‐benzotropolone methyl ether ( 15 ) by sulfoxide formation and pyrolysis; 15 was demethylated with BCl 3 . The same intermediate resulted from the dichlorobenzocycloheptadienone 8 b and NaOMe. The benzocycloheptadienone 10 a was de( tert ‐butylated) with formic acid; a subsequent Pfitzner‐Moffatt oxidation completed 6,7‐benzotropolone ( 6 a ) once more. The PhS‐containing benzocycloheptadienone 10 b was α‐acetoxylated with Pb(OAc) 4 ; the resulting O,S‐acetal gave 6,7‐benzotropolone ( 6 a ) by hydrolysis. The PhSO 2 ‐containing substrate 10 c was deprotonated whereupon an oxidation with Me 3 Si−O−O−SiMe 3 gave 6,7‐benzotropolone ( 6 a )." @default.
• W3208085129 created "2021-11-08" @default.
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• W3208085129 date "2022-02-25" @default.
• W3208085129 modified "2023-10-16" @default.
• W3208085129 title "Syntheses of 6,7‐Benzotropolone Using Ring‐Closing Metathesis Variants, Which Circumvent a Strongly Acidic Hydrolysis in the Sequel" @default.
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• W3208085129 doi "https://doi.org/10.1002/ejoc.202101070" @default.
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