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- W2951657000 abstract "Abstract The total synthesis of the tetrahydroisoindolinone moiety corresponding to proxiphomin ( 1 ) is described, bearing functional groups for the attachment of the macrocyclic ring. Knoevenagel‐Cope condensation of racemic 2‐(benzyloxycarbonyl‐amino)‐3‐phenylpropanal ( 2 ) with methyl (4‐methyl‐2,4‐hexadienyl) malonate ( 3 ) yielded a mixture of the ( E )‐ and ( Z )‐olefins 4a and 4b , which upon heating underwent intramolecular Diels‐Alder cyclization ( cf. Scheme 1 ). From the resulting products the tetrahydroisoindoline derivative 6 was isolated. X‐ray analysis of 6 [5] revealed the same relative configurations at C(3), C(4), C(5) and C(8) as in 1 , but not at C(9). Hydrolysis of 6 with KOH was accompanied by a change in configuration at C(9) yielding the hydroxy acid 14 which was converted into the hydroxy ester 11 ( cf. Scheme 4 ). The presence of a cis ‐anellated lactam ring in 11 has been confirmed by X‐ray analysis of its O ‐acetyl derivative 16 [5]. Ring closure of the hydroxy acid 14 gave the lactone 17 , corresponding to the natural product 1 as to the configuration. The presence of the N ‐benzyloxycarbonyl group in lactone 6 has been shown to be essential for the above‐mentioned ‘inversion’ at C(9), because no configurational change occurred with the N ‐unprotected lactone 8 when treated under the same conditions. The only product obtained was the hydroxy ester 10 possessing the same configuration at C(9) as 8 . Along with stereochemical considerations, mechanistic aspects of the reactions are discussed." @default.
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- W2951657000 date "1981-02-04" @default.
- W2951657000 modified "2023-10-09" @default.
- W2951657000 title "Approaches to the Synthesis of Cytochalasans. Part 3. Synthesis of a substituted tetrahydroisoindolinone moiety possessing the same relative configuration as proxiphomin" @default.
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- W2951657000 doi "https://doi.org/10.1002/hlca.19810640125" @default.
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