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A Stereoselective Synthesis of (±)‐ cis‐γ ‐Irone
Author(s) -
Nussbaumer Cornelius,
Fráter Georg
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710315
Subject(s) - chemistry , stereoselectivity , nonane , double bond , yield (engineering) , derivative (finance) , acrylate , stereochemistry , methyl acrylate , organic chemistry , medicinal chemistry , monomer , polymer , materials science , economics , financial economics , metallurgy , catalysis
Abstract (±)‐ cis‐γ ‐Irone( 1 ), a main constitutent of natural iris oil, has been stereoselectively synthesized from methyl (2 E )‐3 ‐[(2,2,4‐trimethyl‐3‐cyclohexen‐1‐yl)methoxy]‐2‐propenoate (3) (6 steps, overall yield 14%). The cis ‐configuration as the exocyclic position of the double bond of 1 were secured by the thermal ene reaction of the β‐(alkenyloxy)acrylate 3 yielding the 3‐oxabicyclo [3,3,1] nonane derivative 5 .