ISSN:
0947-3440
Schlagwort(e):
Angucyclinones
;
MM 47755
;
X-14881 E
;
Diels-Alder reactions
;
Silicon-oxygen exchange
;
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
The Diels-Alder reactions of the naphthoquinones 1-4 with the dienes 5a-7 were investigated. The regioisomeric outcome of the adducts 10a-10g, 16, and 23 is in agreement with theoretical predictions from frontier orbital calculations. The adduct 10a was further converted to the non-natural (e.g. 15) and the adduct 16 to the natural angucyclinones MM 47755 (19a) and X-14881 E (22) by silicon-oxygen exchange and photooxygenation. The addition of naphtoquinones 2 and 4 to dienes 6 and 7 afford the Diels-Alder adducts 16 and 23, respectively, which are valuable intermediates for further transformation into non-aromatic angucyclinones.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/jlac.1995199508209
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