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Chemoenzymatic Synthesis of an Enantiomerically Enriched Bicyclic Carbocycle Using <i>Candida parapsilosis</i>ATCC 7330 Mediated Enantioselective Hydrolysis

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International Journal of Organic Chemistry 2015年第4期5卷 271-281页

作者： Thangavelu Saravanan Anju Chadha tarur konikkaledom dinesh Namasivayam Palani Sengottuvelan Balasubramanian Laboratory of Bioorganic Chemistry Department of Biotechnology Indian Institute of Technology Madras Chennai India National Center for Catalysis Research Indian Institute of Technology Madras Chennai India Department of Inorganic Chemistry University of Madras Guindy Campus Chennai India ITC Life Sciences and Technology Centre ITC Limited Peenya Industrial Area Phase I Bangalore India

Enantiomerically enriched (R)-1-(2-bromocycloalkenyl)-3-buten-1-ol and its derivatives were obtained via enantioselective hydrolysis [resolution] with good enantioselectivities (E = 31 to >500) using Candida parapsilosis ATCC 7330. The various reaction parameters were optimized for enantioselective hydrolysis to achieve high enantiomeric excess (ee) and conversions. Among the substrates tested, (RS)-1-(2-bromocyclohex-1-en-1-yl) but-3-yn-1-yl acetate was hydrolysed by the biocatalyst in 12 h to the corresponding (R)-alcohol in 49% conversion and >99 ee. The optically pure allylic alcohol thus obtained was used as a chiral starting material for the synthesis of an enantiomerically enriched bicyclic alcohol effectively establishing achemoenzymatic route.

关键词： Chemoenzymatic Synthesis Enantioselective Hydrolysis Candida parapsilosis ATCC 7330 Hydrolases Bicyclic Carbocycle

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A Novel Approach for the Synthesis of (R) and (S)-Nicotine

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International Journal of Organic Chemistry 2022年第4期12卷 189-199页

作者： Rohith Kumar Agarthimoole Sahir Gagan Sudesna Parida tarur konikkaledom dinesh Maheswaran S. Karatholuvhu Namasivayam Palani Soumitra Mukherjee ITC Limited ITC Life Sciences and Technology Centre Peenya Industrial Area Phase I Bangalore India Presently at Department of Atmospheric Sciences Texas A&M University College Station Texas USA

Nicotine is an alkaloid mainly found in leaves of tobacco and is used therapeutically for patients seeking relief from tobacco dependence in the form of products such as gums, patches, lozenges etc. In these products, majorly nicotine derived from tobacco is used which is inherently contaminated with undesirable nicotine related substances as impurities at low levels and is difficult to remove. Hence, use of synthetic nicotine is considered as an option which will be devoid of such impurities. In this work, a short and efficient synthesis of (R) and (S) nicotine was achieved by leveraging a key esterification between racemic homoallylic alcohol intermediate (2) and (S)-Ibuprofen (3) to produce diastereomers (5a) and (5b) which were easily separable under standard column chromatography conditions. Use of (S)-Ibuprofen (3) as a chiral resolving agent constitutes a novel approach which was not reported earlier. A subsequent hydrolysis of the diastereomers furnished the homoallylic alcohol intermediates (S)-6a and (R)-6a with high enantiopurity, which was effectively translated to the corresponding (R)-nicotine and (S)-nicotine respectively.

关键词： Nicotine Ibuprofen Diastereomers Column Chromatography Chiral Purity

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