Total synthesis of (+)-prelog-djerassi lactonic acid |
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Authors: | Minoru Isobe Yoshiyasu Ichikawa Toshio Goto |
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Affiliation: | Laboratory of Organic Chemistry, Faculty of Agriculture, Nagoya University, Chikusa, Nagoya 464, Japan |
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Abstract: | Optically active Prelog-Djerassi Lactonic Acid was synthesized from D-glucal: the crucial point being the elaboration of the carboxylic group as shown in eq. 1 and 2 which involve the sequential process [i] asymmetric addition of methyl anion onto the hetero-olefin 2, [ii] trapping the carbanion intermediate [E=Li to SePh] and [iii] oxidative hydrolysis of sila-pummerer rearrangement into . |
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