P. Rao
May 9, 2018
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Abstract
Polyhydroxylated compounds are ubiquitous structural motifs found in a multitude of naturally occurring compounds, pharmaceuticals and material interest [1-5]. In addition to this their synthetic analogues are important as lead structures or drug candidates for the discovery of novel drugs [6-9]. These compounds have explicitly exhibited a broad spectrum of biological activities including antibacterial, antitumoral, antimicrobial, antifeedant, herbicidal, plant growth inhibition and the inhibition of cholesterol biosynthesis properties [10-14]. Recently Hirokazu Kawagishi et al. isolated the triol compound named (3S,4R)-5-Phenylpentane-1,3,4-triol (1, Scheme 1) from the EtOH extract of edible mushroom Mycoleptodonoides aitchisonii [15]. It exhibits protective activity against endoplasmic reticulum (ER) stress-dependent cell death. ER stress is caused by abnormalities in cell function such as changes in calcium channel functioning or accumulation of misfolded protein and this may be responsible for Parkinson’s, Alzheimer’s and prion type of human neuronal diseases, and also other diseases (diabetes, atherosclerosis, and heart & liver disease) [16,17]. Therefore, development of efficient strategies for the preparation of natural and unnatural products, which exhibits protective activity against endoplasmic reticulum stress-dependent cell death, is of great significance. Due to its interesting structural features and evident pharmacological potential, the synthesis of 1 has attracted much attention for the synthetic and medicinal chemists. In continuation of our research on the synthesis of biologically significant natural products from simple starting materials [18,19]. We herein, report a first total synthesis of 1, starting from 3-phenylpropanal (2) in a six steps with 45% overall yield. Abstract