A Stereoselective Synthesis of (±)‐ cis‐γ ‐Irone | Zendy

Nussbaumer Cornelius | Zendy; Fráter Georg | Zendy

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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

(±)‐ 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 .

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