By John ApSimon
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Extra info for The Total Synthesis of Natural Products. Volume 1
DL-eryt/iro-hexose, although the latter compound was not Fully characterized. Other examples of the stereoselective hydroxylation of double bonds by osmic acid were provided by the total synthesis of 4-O-methyl-~~-lyxose and 4-deoxy-~~-ribose~~O (see Scheme 42). -~~-erythro-pentopyranoside (124) and methyl 0 - # oso, ni-CIC, H,COIH dioxane or pyridine 111 0 109 1 1 IN HCI, LiAIH, @ 122 OtI 120 dloxanc INHCI CH,OH dioxanc 123 Scheme 41 HRo CH,OH 121 6. Syntheses from Furan and Pyran Derivatives OCH, It R=H R = CH,O 47 OCH 124 R = H 125 R = CH,O 126 R = H 127 R = CH,O Scheme 42 4-O-methyl-a-~~-lyxopyranoside (125), respectively.
Thus, for example, heating trans-85 (a product of the condensation of l-acetoxy-l,3-butadiene with butyl glyoxylate) in acetic anhydride gave two new products, the butyl esters of trans- and cis-4-acetoxy-5,6-dihydro-4H-pyran 6-carboxylic acid (86). The isomerization could be reversed, when cis- or truns-86 were heated in acetic anhydride: OAc 85 86 Much progress has been made in recent years by Brown and his associates in Canada toward the total syntheses, involving pyran intermediates, of monosaccharides.
L]octane (107 72 109 Scheme 38 I10 44 The Total Synthesis of Carbohydrates and 108). Heating the mixture of 107 and 108 in refluxing ethanolic potassium hydroxide gave the two olefins 109 and 110, which were readily separated by gas-liquid chromatography; the proportion of the two isomeric olefins obtained depended upon the proportion of base to monobromide used during dehydrohalogenation. l]oct-3-ene(109) and its isomer 110 have been used for the synthesis of several monosaccharides and their derivatives.
The Total Synthesis of Natural Products. Volume 1 by John ApSimon