By John ApSimon
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Extra resources for The Total Synthesis of Natural Products. Volume 1
Forosamine has been obtained from the acid hydrolysate of spiramycin. The second synthesisll' of a derivative of kasugamine involved 3,4dihydro-2-ethoxy-6-methyl-2H-pyran (138). Hydroboration of 138, followed by treatment with chloramine, gave the amine 162, which was isolated as the acetylated derivative 163 (see Scheme 48). Treatment of 163 with bromine 161 6. Syntheses from Furan and Pyran Derivatives 53 containing hydrogen chloride yielded three bromo compounds, 164, 165, and 166; both of the isomers 165 and 166 could be converted into 164.
L]oct-3-ene(109) and its isomer 110 have been used for the synthesis of several monosaccharides and their derivatives. Compound 111was converted into 1,6-anhydro3,4-dideoxy-~-~~-eryrkro-hex-3-enopyranose (114, R = H) with n-butyllithium. Treatment of 114 with rn-chloroperoxybenzoic acid gave 1,6: 3,4dianhydro-p-m-ah-hexopyranose (119, which with aqueous barium 112 111 OH 113 Scheme 39 6. -~~-gluco-hexopyranose (116). Acid-catalyzed hydrolysis of 116 afforded a,@-DL-glucose(117). 3-@Methylhave also been obtained107a m-glucose and 3-deoxy-~~-ribo-hexopyranose from compound 115.
2,3-Dihydroxy-tetrahydropyranand -tetrahydrofuran can be made from the dihydropyran 70 and the dihydrofuran 69 by reaction with osmium CH20CH3 H2C OCH3 + C H , O H -@+ H % OCH, trans (70%) +% CH2OCH3 OCH3 H cis (30%) Scheme 25 tetroxide and hydrogen peroxide in t-butan0177 or with lead tetraacetate,BB respectively. Both diols give 2,4-dinitrophenylosazones. In a more recent study,78 70 was treated with m-chloroperoxybenzoic acid in wet ether to give a diol (Scheme 26) whose NMR spectrum indicated it to be a mixture of the cis and trans isomers in the ratio of 30: 70, respectively.