1,4-Addition von carbanionen an pyranosid-enone

Paulsen, Hans; Koebernick, Wolfgang; Koebernick, Hubert

doi:10.1016/s0040-4039(00)78760-0

Cited by 25 publications

(3 citation statements)

References 10 publications

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“…Treatment of enone 8 with an excess of benzyl alcohol in the presence of potassium carbonate gave ketone 9 . The addition should occur on the face trans to the anomeric substituent . The expected configuration at C-2 of the ketone 9 was consistent with 1 H NMR data and was unequivocally confirmed at the next step of the synthesis by single-crystal X-ray analysis (vide infra) of its derivative.…”

Section: Resultssupporting

confidence: 72%

“…The addition should occur on the face trans to the anomeric substituent. 20 The expected configuration at C-2 of the ketone 9 was consistent with 1 H NMR data and was unequivocally confirmed at the next step of the synthesis by single-crystal X-ray analysis (vide infra) of its derivative. The introduction of the benzyloxy substituent at C-2 served yet another purpose: activation of the C-1-C-2 bond for future scission.…”

Section: Resultssupporting

confidence: 66%

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New Chiral Pool Approach to Anthracyclinones. The Stereoselective Synthesis of Idarubicinone

Achmatowicz

Szechner

2003

J. Org. Chem.

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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 ketoacetals 25 and 26 to which 3-cyano-1(3H)-isobenzofuranone 27 was annelated. Removal of the isopropylidene group in the resulting 28, subsequent oxidation of the C(13) hydroxyl and full deprotection led to idarubicinone (4).

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Section: Resultssupporting

confidence: 72%

Section: Resultssupporting

confidence: 66%

New Chiral Pool Approach to Anthracyclinones. The Stereoselective Synthesis of Idarubicinone

Achmatowicz

Szechner

2003

J. Org. Chem.

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“…( 5 ) ist aus ( 1 1 ) oder besser aus (2) darstellbar. Das Entschwefelungsprodukt (3) von (2) reagiert mit LiAIH4 in der Seitenkette selektiv, nicht dagegen am Epoxidring, so daR (4) und ( 5 ) entstehen.…”

Section: Synthese Der Y-octdse Des Chinocyclin-komplexe[**]unclassified