Synthesis of the tetracyclic core of anthracycline antibiotics by an intramolecular dehydro diels-alder approach

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3119-3121

  Rodríguez, David ^a   Castedo, Luis ^a   Domínguez, Domingo ^a   Saá, Carlos ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

7,8,9,10 TETRAHYDRONAPHTHACENE 5,12 DIONE; ANTHRACYCLINE ANTIBIOTIC AGENT; NAPHTHACENE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

ANTHRACYCLINES; ANTIBIOTICS, ANTINEOPLASTIC;

EID: 0141743689     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035168e     Document Type: Article

References (29)

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24. Synthesis of the related benzo[a]anthracene nucleus and its application to the synthesis of angucyclinone antibiotics has been recently reported, being the key step in the simultaneous formation of three rings via a cobalt-mediated [2+2+2] cycloaddition of a triyne: Kalogerakis, A.; Groth, U. Org. Lett. 2003, 5, 843-844. Straub, H.; Hambrecht, J. Synthesis 1975, 425-426.
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26. The side products may have arisen, in part, from reaction with oxygen present in the solvent. When the toluene was degassed prior to use, the yields of 7 and 8 decreased to 6% and 2%, respectively. Assignment of the structures was supported by the observation of an HMBC correlation between the ketone of the carbonyl group and the singlet corresponding to the hydrogen placed in the peri position.
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