Primary and Secondary Allyltitanium(IV) Reagents in Aldehyde Allylation II: Application to an Enantioselective Preparation of a C1-C7 Fragment of Spiramycin

Patrick Razon; Marie-Ange N’Zoutani; Sylvie Dhulut; Sophie Bezzenine-Lafollée; Ange Pancrazi; Janick Ardisson

doi:10.1055/s-2004-834913

PAPER

Primary and Secondary Allyltitanium(IV) Reagents in Aldehyde Allylation II: Application to an Enantioselective Preparation of a C1-C7 Fragment of Spiramycin

Patrick Razon, Marie-Ange N’Zoutani, Sylvie Dhulut, Sophie Bezzenine-Lafollée, Ange Pancrazi, Janick Ardisson*
Laboratoire de Synthèse Organique Sélective et Chimie Organométallique, CNRS-UCP-ESCOM, UMR 8123, ESCOM, Bat E, 13 Bd de l’Hautil, 95092 Cergy-Pontoise, France
Fax: +33(1)307561; e-Mail: janick.ardisson@chim.u-cergy.fr;

Abstract

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Abstract

A synthetic approach to the eastern part of spiramycin, an important antibiotic compound, is described. Introduction of the side chain was first envisaged through a Hoppe aldehyde allylation. This reaction was carried out between an optically pure aldehyde 32 and a (±)-γ-alkoxy allyltitanium(IV) species derived from a primary γ-alkoxy allyl (diisopropyl)carbamate. Under kinetic resolution conditions, the anti-Cram compound 35 was obtained in an 80:20 mixture, with the Cram isomer 34, in 81% yield. Employing the optically pure (S)-γ-alkoxy allyl (diisopropyl)carbamate 36, the corresponding (R)-γ-alkoxy allyltitanium (R)-‘Ti’-III was generated under n-BuLi·TMEDA/Ti(Oi-Pr)₄conditions, that reacted with aldehyde 32 in double stereodifferentiation to deliver the expected Cram compound 40 in 80% yield (95% de). This latter corresponded to the C1-C7 fragment of spiramycin.

Key words

spiramycin - synthesis - Hoppe allylation - secondary allyltitanium reagent - double stereodifferentiation

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References

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