1993
DOI: 10.1002/recl.19931121008
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Reactions of thebaine and 6‐demethoxythebaine anions with carbonyl compounds; novel Diels‐Alder adducts from 5β‐substituted thebaines (chemistry of opium alkaloids, Part XXXIX)

Abstract: Abstract. Reaction of the anions of thebaine and 6-demethoxythebaine with 2-propanone gave the 5~-(dirnethylmethanoI)-substituted analogues 3 and 5 and the isomeric C-7-substituted morphinan-5,8-dienes 4, 6 and 7 , respectively. N o reaction took place with methanal. Therefore, thebaine-5P-methanol (10) was prepared by reacting the anion with alkyl chloroformate followed by lithium aluminium hydride reduction. Diels-Alder reaction of diene 10 with ethyl acrylate gave the 6a,l4a-ethenoisomorphinan 11. Of the mo… Show more

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Cited by 6 publications
(5 citation statements)
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“…They found that the main product of the reaction is in fact 7 -methyl-5,8-morphinandiene (42a) [89]. This ring system and the electronic configuration of ring C could be considered as a transition between the 4,5-epoxy ring-opened salutaridinol (7) and 6,8-morphinandienes.…”
Section: -Methyl-6-demethoxythebaine and The Occurrence Of 58-typementioning
confidence: 98%
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“…They found that the main product of the reaction is in fact 7 -methyl-5,8-morphinandiene (42a) [89]. This ring system and the electronic configuration of ring C could be considered as a transition between the 4,5-epoxy ring-opened salutaridinol (7) and 6,8-morphinandienes.…”
Section: -Methyl-6-demethoxythebaine and The Occurrence Of 58-typementioning
confidence: 98%
“…Maat and his co-workers prepared the 7-chloro-5 -methyl-6-demethoxythebaine (89) and performed detailed study of the stereochemistry of Diels-Alder reaction of this 5,7-disubstituted diene [96]. Starting from 5 -methylthebaine (74) they obtained 7-methoxy-5 -methyl-6-demethoxythebaine (91) via its 7-(methoxymethoxy)-congener 90 (Scheme 34) [124,125].…”
Section: Other Disubstituted Morphinandienesmentioning
confidence: 99%
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“…Woudenberg et al [62] performed the Diels-Alder reaction of thebaine-5β-methanol (12d, Figure 17) with ethyl acrylate, concluding that introduction of a hydroxymethyl group in the 5β position of thebaine had no influence on the face selectivity of the cycloaddition. Boiling 12d with ethyl acrylate for one week resulted in exclusively the corresponding 7α-ethoxycarbonyl-6α,14α-etheno-adduct (51, 50% conversion, 41% isolated yield, β-face addition).…”
Section: β-Alkylthebainesmentioning
confidence: 99%