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Superacid cyclization of (2E,6E,10E,14E)-8-phenylsulfonylgeranylfarnesol tetrahydropyranyl ether

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Abstract

A mixture of (13E,17E)-12-phenylsulfonylbicyclogeranylfarnesol tetrahydropyranyl ether (8) and (13E,17E)-12-phenylsulfonylbicyclogeranylfarnesol (9) was formed by superacid low-temperature cyclization of exclusively trans-8-phenylsulfonylgeranylfarnesol tetrahydropyranyl ether (1). The structures of 8 and 9 were established using spectral data. The optically active form of 9 was also confirmed by retrosynthesis from (+)-sclareolide (10).

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Authors and Affiliations

  1. Institute of Chemistry, Academy of Sciences of Moldova, ul. Akademii, 3, MD 2028, Kishinev, Republic of Moldova

    V. Kulcitki, M. Grin’ko, A. Barba, N. Ungur & P. F. Vlad

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  1. V. Kulcitki
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  2. M. Grin’ko
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  3. A. Barba
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  4. N. Ungur
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  5. P. F. Vlad
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Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 224–228, May–June, 2007.

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Kulcitki, V., Grin’ko, M., Barba, A. et al. Superacid cyclization of (2E,6E,10E,14E)-8-phenylsulfonylgeranylfarnesol tetrahydropyranyl ether. Chem Nat Compd 43, 268–273 (2007). https://doi.org/10.1007/s10600-007-0102-5

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  • DOI: https://doi.org/10.1007/s10600-007-0102-5

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