2003
DOI: 10.1021/jo026354l
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New Chiral Pool Approach to Anthracyclinones. The Stereoselective Synthesis of Idarubicinone

Abstract: In the present work, a new chiral pool approach has been developed for the synthesis of anthracyclinones. Thus, enone 8, readily available from l-rhamnose, has been converted via addition of 2,5-dimethoxybenzyllithium to the carbonyl group and a series of six reactions into a suitably protected aldehyde 21. The SnCl(4)-promoted stereospecific cyclization of the latter afforded enantiopure key intermediate 22. Silylation of benzylic hydroxyl of 21 followed by anodic oxidation and selective hydrolysis gave ketoa… Show more

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Cited by 21 publications
(9 citation statements)
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“…The title compound, (I), is an intermediate in the enantioselective synthesis of an anthracycline-like product. Compound (I) possesses obvious similarities to both idarubicin (II) and daunorubicin (III), and the stereochemistry of the stereogenic centers at C3 and C1 are exactly identical to that of the anthracycline antibiotics (Chen & Liu, 1994;Champoux, 2001;Achmatowicz & Szechner, 2002). The product was obtained in reasonable yield and diastereoselectivity (80% yield, 74% d.e.)…”
Section: Commentmentioning
confidence: 93%
“…The title compound, (I), is an intermediate in the enantioselective synthesis of an anthracycline-like product. Compound (I) possesses obvious similarities to both idarubicin (II) and daunorubicin (III), and the stereochemistry of the stereogenic centers at C3 and C1 are exactly identical to that of the anthracycline antibiotics (Chen & Liu, 1994;Champoux, 2001;Achmatowicz & Szechner, 2002). The product was obtained in reasonable yield and diastereoselectivity (80% yield, 74% d.e.)…”
Section: Commentmentioning
confidence: 93%
“…53 Hydroxyphthalides are intermediates for assembly of anthracyclinone-type antibiotics. 54 Of special interest is the ability of the carboxylate to introduce an allyl substituent. Reaction of N,N-diisopropylbenzamide or 2-methoxy-N,N-diethylbenzamide with allyl bromide under standard conditions (s-BuLi-TMEDA complex, -78 °C, THF) provided the bromides instead of the allylated derivatives.…”
Section: Resultsmentioning
confidence: 99%
“…In cases where DoM occurs at the position adjacent to the carboxylate group (routes A, C, and F), the primary products obtained with DMF ( 4 , 6 , 9 g ) and benzaldehyde ( 4 , 6 , 9h ) after acidic hydrolysis were directly transformed into hydroxyphthalides and lactones 11 − 16 (Figure ) . Hydroxyphthalides are intermediates for assembly of anthracyclinone-type antibiotics 4 Hydroxyphthalides and lactones 11 − 16 .…”
Section: Resultsmentioning
confidence: 99%
“…Methods for carrying out this transformation include oxidation by using ceric ammonium nitrate (CAN), [16] hypervalent iodine reagents [20] or anodic methods. [21] Initial efforts in this area have been fruitful with the successful CAN oxidation of compound rac-20.…”
Section: Resultsmentioning
confidence: 99%