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Short Paper | Special issue | Vol 99, No. 1, 2019, pp.716-723
Published online, 17th October, 2018
DOI: 10.3987/COM-18-S(F)44
Concise Synthesis of Anticancer Active trans-4-(4-Octylphenyl)prolinol

Junki Ando, Aoi Tazawa, Kohei Ishizawa, Minoru Tanaka,* and Hiroyoshi Takamura*

*Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

Concise synthesis of anticancer active trans-4-(4-octylphenyl)prolinol has been achieved. Regioselective iodination of aromatic compound and subsequent Suzuki–Miyaura cross-coupling with trans-1-octen-1-ylboronic acid produced the desired coupling product. Further transformation of this product afforded trans-4-(4-octylphenyl)prolinol. The synthesis of this anticancer compound has been performed with 23% overall yield and six steps, which have been improved in comparison with those (3.5% overall yield and eight steps) previously reported.