The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (S)-Methyl 3-hydroxybutanoate( cas:53562-86-0 ) is researched.Formula: C5H10O3.Kobayashi, Yuichi; Kumar, G. Biju; Kurachi, Tomoaki; Acharya, Hukum P.; Yamazaki, Takashi; Kitazume, Tomoya published the article 《Furan Ring Oxidation Strategy for the Synthesis of Macrosphelides A and B》 about this compound( cas:53562-86-0 ) in Journal of Organic Chemistry. Keywords: furan ring oxidation macrosphelide A B synthesis. Let’s learn more about this compound (cas:53562-86-0).
By using the convenient protocol for conversion of 2-substituted furans into 4-oxo-2-alkenoic acids ((i) NBS, (ii) NaClO2), macrosphelide B (I, R = H) was synthesized from furyl alc. II (>98% ee) and (S)-Me3CSiMe2OCHMeCH2CO2H (99% ee). Key steps include condensation of (2E,5S)-5-(4-methoxybenzyloxy)-4-oxo-2-hexenoic acid with the furylmethyl ester III and intramol. cyclization of the adduct IV to I (R = MeOCH2). Transformation of I (R = MeOCH2) to macrosphelide A was then investigated. Although the chelation-controlled reduction of I (R = MeOCH2) should afford the desired anti alc., Zn(BH4)2 at <-90 °C gave a 2∼1:1 mixture of anti/syn alcs. On the contrary, reduction with NaBH4 in MeOH at -15 °C produced the syn isomer with >10:1 diastereoselectivity. Mitsunobu inversion of the resulting C(14)-hydroxyl group and deprotection of the MOM group with TFA afforded macrosphelide A. Similarly, reduction of I (R = H) with NaBH4 afforded the C(14)-epimer of macrosphelide A stereoselectively. The observed stereoselectivity in the reductions of I could be explained on the basis of computer-assisted calculation, which showed presence of the low-energy conformers responsible for the stereoselective reduction In addition, conversion of I (R = H) to macrosphelide A was established, for the first time.
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Reference:
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