Paper
Study on synthesis of (R)-tert-butyl 4-formyl-2,2-dimethylthiazolidine-3-carboxylate
Published Jan 1, 2016 · Shen K. Yang, Shuanglin Qin, Xiaoji Wang
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Abstract
(R)-tert-butyl 4-formyl-2,2-dimethylthiazolidine-3-carboxylate is an imntermediate of S-jaspine B known as a potential substitution of pachastrissamine (jaspine B) which shows effective biological activity. Herein we describe an elegant straightforward synthetic path for this attractive molecule intermediate. Introduction Jaspine B (1) (showed in Figure 1) is a natural occurring product with three chiral centers in a tetrahydrofuran ring. Since jaspine B has been firstly isolated form Okinawan marine sponge Pachastrissa sp. in 2002 by Higa and coworkers [1], many investigations has been attached to this attractive molecule and its analogs [2-4]. Jaspine B was observed to display remarkable cytotoxicity against several kinds of cancer cell lines. Andrieu-Abadie and co-workers reported that jaspine B induces apoptotic cell death in melanoma cells through a caspase-dependent pathway [5]. A lot of literatures have reported the syntheses of jaspine B [6-9].
This study presents a straightforward synthetic path for (R)-tert-butyl 4-formyl-2,2-dimethylthiazolidine-3-carboxylate, a potential substitute of pachastrissamine (jaspine B) with effective biological activity against various cancer cell lines.
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