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A Stereoselective Synthesis of (±)-cis-γ-Irone (1988)

Nussbaumer, Cornelius ; Fráter, Georg

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 71 (1988), S. 619-623

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: (±)-cis-γ-Irone(1), a main constitutent of natural iris oil, has been stereoselectively synthesized from methyl (2E)-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.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19880710315

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