Abstract
A series of Diels-Alder adducts has been synthesised from 4a,9a-epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetraone (5), and the naphthacene (9b) has subsequently been converted into the epoxides (9d) and (9e). Catalytic hydrogenolysis of the ethanonaphthacene (9a) gave after work-up in air the 6,11 -dione (11), whereas hydrogenolysis of the methanonaphthacene (9f) gave a condensed leuco quinizarin derivative (13). Catalytic hydrogenolysis of the ethylenedioxynaphthacene (9e) gave the partially reduced trihydroxy derivative (15), the structure of which was established by converting it in two steps into the known trione (6a). Compound (9e) was also transformed oxidatively into the condensed quinizarin derivative (16), and by base-promoted methylation into a compound believed to be the dione (6d); the latter was deprotected to give the trione (6e).
| Original language | English |
|---|---|
| Pages (from-to) | 39-43 |
| Number of pages | 5 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Publication status | Published - 1985 |
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Synthesis of intermediates related to 11-deoxyanthracyclinones. / Preston, Peter N.; Winwick, Thomas; Morley, John O.
In: Journal of the Chemical Society, Perkin Transactions 1, 1985, p. 39-43.Research output: Contribution to journal › Article
TY - JOUR
T1 - Synthesis of intermediates related to 11-deoxyanthracyclinones
AU - Preston, Peter N.
AU - Winwick, Thomas
AU - Morley, John O.
PY - 1985
Y1 - 1985
N2 - A series of Diels-Alder adducts has been synthesised from 4a,9a-epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetraone (5), and the naphthacene (9b) has subsequently been converted into the epoxides (9d) and (9e). Catalytic hydrogenolysis of the ethanonaphthacene (9a) gave after work-up in air the 6,11 -dione (11), whereas hydrogenolysis of the methanonaphthacene (9f) gave a condensed leuco quinizarin derivative (13). Catalytic hydrogenolysis of the ethylenedioxynaphthacene (9e) gave the partially reduced trihydroxy derivative (15), the structure of which was established by converting it in two steps into the known trione (6a). Compound (9e) was also transformed oxidatively into the condensed quinizarin derivative (16), and by base-promoted methylation into a compound believed to be the dione (6d); the latter was deprotected to give the trione (6e).
AB - A series of Diels-Alder adducts has been synthesised from 4a,9a-epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetraone (5), and the naphthacene (9b) has subsequently been converted into the epoxides (9d) and (9e). Catalytic hydrogenolysis of the ethanonaphthacene (9a) gave after work-up in air the 6,11 -dione (11), whereas hydrogenolysis of the methanonaphthacene (9f) gave a condensed leuco quinizarin derivative (13). Catalytic hydrogenolysis of the ethylenedioxynaphthacene (9e) gave the partially reduced trihydroxy derivative (15), the structure of which was established by converting it in two steps into the known trione (6a). Compound (9e) was also transformed oxidatively into the condensed quinizarin derivative (16), and by base-promoted methylation into a compound believed to be the dione (6d); the latter was deprotected to give the trione (6e).
M3 - Article
SP - 39
EP - 43
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 1472-7781
ER -