A Total Synthesis of (-)-Nardoaristolone B

Ople, Rohini S. ; Handore, Kishor L. ; Kamat, Nidhi S. ; Srinivasa Reddy, D. (2016) A Total Synthesis of (-)-Nardoaristolone B European Journal of Organic Chemistry, 2016 (22). pp. 3804-3808. ISSN 1434-193X

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Official URL: http://doi.org/10.1002/ejoc.201600538

Related URL: http://dx.doi.org/10.1002/ejoc.201600538

Abstract

A stereoselective total synthesis of (–)-Nardoaristolone B, a nor-aristolane sesquiterpenoid natural product with an unusual 3/5/6 tricyclic ring system is described. The highlights of the present work includes use of (+)-(R)-Pulegone as a chiral-pool starting material, ring-closing metathesis, allylic oxidation and stereoselective cyclopropanation. In addition, a new analogue of Nardoaristolone B (minor product from the final step) was isolated in pure form and fully characterized with the help of single-crystal X-ray analysis.

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Deposited On:23 Jul 2021 08:48
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