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A Total Synthesis of (–)‐Nardoaristolone B
Author(s) -
Ople Rohini S.,
Handore Kishor L.,
Kamat Nidhi S.,
Srinivasa Reddy D.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600538
Subject(s) - total synthesis , chemistry , stereoselectivity , pulegone , cyclopropanation , metathesis , ring closing metathesis , stereochemistry , allylic rearrangement , natural product , salt metathesis reaction , ring (chemistry) , organic chemistry , catalysis , polymer , chromatography , essential oil , polymerization
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.