85178-50-3Relevant articles and documents
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Kuntsmann,M.P.,Mitscher,L.A.
, p. 2920 - 2925 (1966)
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A unified strategy for the syntheses of angucyclinone antibiotics: Total syntheses of tetrangulol, kanglemycin M, X-14881-E, and anhydrolandomycinone
Vanga, Devendar Goud,Kaliappan, Krishna P.
, p. 2250 - 2259 (2012/06/18)
A unified strategy for the syntheses of angucyclinone antibiotics was developed utilizing sequential intramolecular enyne metathesis, Diels-Alder/aromatization, photooxygenation, and one-pot elimination/ aromatization reactions. The diversity in this sequ
Synthesis of Naturally (MM 47755; X-14881 E) and Non-Naturally Occuring Aromatic Angucyclinones
Krohn, Karsten,Khanbabaee, Karamali,Micheel, Joerg
, p. 1529 - 1538 (2007/10/02)
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 naphthoquinones 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. - Keywords: Angucyclinones / MM 47755 / X-14881 E / Diels-Alder reactions / Silicon-oxygen exchange