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Studies Towards The Synthesis Of Marine Alkaloid (+)-cylindricine | 7481
ISSN: 2167-7689

Pharmaceutical Regulatory Affairs: Open Access
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Studies towards the synthesis of marine alkaloid (+)-cylindricine

2nd International Conference and Exhibition on Pharmaceutical Regulatory Affairs

V. N. S. Murali Rampalli and S. Chandrasekhar

Posters: Pharmaceut Reg Affairs

DOI: 10.4172/2167-7689.S1.007

Cylindricine was isolated from the marine ascidian (sea squirt) Clavelina cylindrica, It possesses a tricyclic skeleton with pyrrolo[2,1-j]quinoline framework. Cylindricine was found to be potent as a toxin. Here in we are reporting the synthesis of bicyclic quinolizidine moiety bearing a quaternary centre which is the key intermediate to achieve the total synthesis of Cylindricine. Heptanaldehyde was subjected to enantioselective Keck allylation to furnish the (S)-dec-1-en-4-ol, which was converted to its mesylate compound using MsCl and triethylamine. Displacement of the ?OMs group with NaN3 provided (R)-4-azidodec-1-ene, followed by the reduction with LiAlH4 to furnish it?s amine and then converted to it?s t-Butyl carbamate, further subjected to one pot osmylation to afforded (R)-tert-butyl 1-oxononan-3-ylcarbamate. The aldehyde functionality underwent aldol reaction with cyclohexanone in presence of L-Proline as catalyst to give inseparable diastereomeric mixture of β-hydroxy ketones in 7:3 ratio which were separated by making their acetyl-derivatives (anti:syn = 7:3) and then deacetylated to give tert-butyl (1S,3R)-1-hydroxy-1-((S)-2-oxocyclohexyl)nonan-3-ylcarbamate, followed by treatment with TFA furnished an intramolecular imine, that undergoes a Barbier type allylation, to give the quinolizidine moiety bearing a quaternary centre. The free amine of this quinolizidine, was protected as its carbobenzyloxy ether. Scheme 1: Retrosynthetic Analysis of Cylindricine
V. N. S. Murali obtained his Masters in Chemistry in the year 2006 from Andhra University. He specializes in synthesis of Natural products and bioactive small molecules. He is a Senior Research Fellow under CSIR and presently he is a researcher in the field of Natural products synthesis with Indian Institute of Chemical Technology-Hyderabad. He has 2 research articles published international journals to his credit. He has attended more than 8 national and international conferences.
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