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1: Bioorg Med Chem Lett. 2002 Nov 18;12(22):3313-5.Click here to read Links

Intramolecular aldol cyclization of L-lyxo-hexos-5-ulose derivatives: a new diastereoselective synthesis of D-chiro-inositol.

Catelani G, Corsaro A, D'Andrea F, Mariani M, Pistarà V.

Dipartimento di Chimica Bioorganica e Biofarmacia, Università degli Studi di Pisa, Via Bonanno, 33, I-56126 Pisa, Italy. giocate@farm.unipi.it

The DBU-promoted intramolecular aldol condensation of two partially protected L-lyxo-hexos-5-ulose derivatives (8 and 9), in turn obtained starting from methyl beta-D-galactopyranoside, takes place with fairly good yield and complete diastereoselectivity to give 2L-(2,3,6/4,5)-pentahydroxycyclohexanone derivatives, 10 and 11. The stereoselective reduction of inosose 10 with sodium triacetoxyborohydride leads, after catalytic debenzylation, to D-chiro-inositol (1), while the sodium borohydride reduction furnishes, with opposite stereoselectivity, a derivative of allo-inositol.

PMID: 12392740 [PubMed - indexed for MEDLINE]