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Asymmetric synthesis of (+)-trachyspic acid

✍ Scribed by Kenji Morokuma; Yuko Taira; Yumiko Uehara; Setsuya Shibahara; Keisuke Takahashi; Jun Ishihara; Susumi Hatakeyama

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 189 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.07.004

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✦ Synopsis

Aldol reaction of di-tert-butyl 4-(4-methoxybenzyloxy)-2-oxobutanoate with pent-4-enal using (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride as a catalyst, followed by Pinnick oxidation and tert-butyl esterification, gave (2S,3S)-di-tert-butyl 2-(2-(4-methoxybenzyloxy)ethyl)-3-allyl-2-hydroxysuccinate in high optical purity (85% ee), from which the total synthesis of (+)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished.

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