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 b-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.
Intramolecular aldol cyclization of L-lyxo-hexos-5-ulose derivatives: a new diastereoselective synthesis of D-chiro-inositol
CATELANI, GIORGIO;D'ANDREA, FELICIA;
2002-01-01
Abstract
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 b-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.File in questo prodotto:
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