Erythritol 2,3-anhydro-, synthesis

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The synthesis began with the treatment of 3,4-anhydro-l,2-0-isopropylidene-D-erythritol 90 with 2-alkyl-2-lithio-l,3-dithiane 92 to give 93 (Scheme 16). Reductive desulfurization of 93 and transacetalization of the resulting 94 by the following reaction sequence (1. acidic hydrolysis 2. protection of the primary hydroxyl group 3. ketalization and 4. basic hydrolysis) afforded the primary alcohol 95. The Swern oxidation of 95 yielded the aldehyde 96. 

Substrates of this type were utilized for the synthesis of alditols. Schneider and co-workers prepared from trans and cis 2-buten-1,4-diols 2,3-anhydro-DL-erythritol (54) and -threitol (55) by direct epoxidation with peroxybenzoic acid. This method of epoxide formation failed in the case of 2 ,4 -hexadiene-l,6-diol from the 2Z,4Z isomer the corresponding diepoxide (57) was obtained in a 2% yield only. However, from 1,6-dibromo-and 1,6-dibenzyloxycarbonyloxy-2 ,4 -hexadienes the corresponding derivatives of 2,3 4,5-dianhydro-DL-gal-actitol (56) could be obtained in moderate yields. Compounds of this type are active against some forms of sarcoma. 

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