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Compound - 1S2R-grandisol [(1S,2R)-cis-2-Isopropenyl-1-methylcyclobutaneethanol]

Bedoukain RussellIPM
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Formula: C10H18O 
MW: 154.25 

[MS]  [Behavioural function

Dots surface:

Reference(s) for synthesis of (1S,2R)-cis-2-Isopropenyl-1-methylcyclobutaneethanol [1S2R-grandisol]

Ayer, W.A., and Browne, L.M. 1974. The transformation of carvone into racemic grandisol. Can J. Chem. 52:1352-1360.
Babler, J.H. 1975. Base-promoted cyclization of a delta-chloro ester: application to the total synthesis of ()-grandisol. Tetrahedron Lett. 16:2045-2048.
Billups, W.E., Cross, J.H., and Smith, C.V. 1973. A synthesis of ()-grandisol. J. Am. Chem. Soc. 95:3438-3439.
Cargill, R.L., and Wright, B.W. 1975. A new fragmentation reaction and its application to the synthesis of ()-grandisol. J. Org. Chem. 40:120-122.
Demuth, M., Palomer, A., Sluma, H.-D., Dey, A.K., Krueger, C., and Tsay, Y.-H. 1986. Asymmetric photocycloadditions with optically pure, spirocyclic enones. Simple synthesis of (+)- and (-)-grandisol. Angew. Chem. Int. Ed. Engl. 25:1117-1119.
Grandjuillot, J.-C., and Rouessac, F. 1973. Sur une voie d'acces a l'isoprenyl-2-methyl-1-cyclobutane ethanol. C.R. Acad. Sci. (Paris). 277:1253.
Gueldner, R.C., Tumlinson, J.H., Hardee, D.D., Thompson, A.C., Hedin, P.A., and Minyard, J.P. 1971. Identification and synthesis of the four compounds comprising the boll weevil sex attractant. J. Org. Chem. 36:2616-2621.
Hobbs, P.D., and Magnus, P.D. 1974. Synthesis of optically active grandisol. J. Chem. Soc. Chem. Comm. 21:856-857.
Hobbs, P.D., and Magnus, P.D. 1976. Studies on terpenes. IV. Synthesis of optically active grandisol, the boll weevil pheromone. J. Am. Chem. Soc. 98:4594-4600.
Jones, J.B., Finch, M.A.W., and Jokotac, I.J. 1982. Enzymes in organic synthesis. XXVI. Synthesis of enantiomerically pure grandisol from an enzyme-generated chiral synthon. Can. J. Chem. 60:2007.
Katzenellenbogen, J.A. 1976. Insect pheromone synthesis: new methodology. Science. 194:139-148.
Kosugi, H., Sekiguchi, S., Sekita, R., and Uda, H. 1976. Photochemical cycloaddition of alpha,-unsaturated lactones with olefins, and application to synthesis of natural products. Bull. Chem. Soc. Jpn. 49:520.
Meyers, A.I., and Fleming, S.A. 1986. Efficient asymmetric (2+2) photocycloaddition leading to chiral cyclobutanes. Application to the total synthesis of (-)-grandisol. J. Am. Chem. Soc. 108:306-307.
Mori, K. 1978. Synthesis of the both enantiomers of grandisol, the boll weevil pheromone. Tetrahedron. 34:915-920.
Mori, K., and Miyake, M. 1987. A new synthesis of both the enantiomers of grandisol, the boll weevil pheromone. Tetrahedron. 43:2229-2239.
Mori, K., Tamada, S., and Hedin, P.A. 1978. (-)-grandisol, the antipode of the boll weevil pheromone, is biologically active. Naturwissenschaften. 65:653-654.
Romming, C., Skattebol, L., and Stenstrom, Y. 1986. 1,4,4-trimethylbicyclo[3.2.1]heptane-3-one. A key intermediate in the synthesis of ()-grandisol, a sex pheromone component of the boll weevil Anthonomus grandis. Acta Chem. Scand. B40:434.
Rosini, G., Geier, M., Marotta, E., Petrini, M., and Ballini, R. 1986. Stereoselective total synthesis of racemic grandisol via 3-oximino-1.4.4-trimethylbicyclo[3.2.0]heptane, an improved practical procedure. Tetrahedron. 42:6027-6032.
Rosini, G., Marotta, E., Petrini, M., and Ballini, R. 1985. Stereoselective total synthesis of racemic grandisol. An improved convenient procedure. Tetrahedron. 41:4633-4638.
Rosini, G., Salomoni, A., and Squarcia, F. 1979. A new, convenient preparation of cis-()-2-acetyl-1-methylcyclobutane-acetic acid, a new intermediate in the synthesis of ()-grandisol. Synthesis. 12:942-943.
Sonawane, H.R., Nanjundiah, B.S., and Kumar, M.U. 1984. Synthesis of ()-grandisol from (+)-delta2-carene: an application of photo-induced vinylcyclopropane rearrangement. Tetrahedron Lett. 25:2245-2246.
Stork, G., and Cohen, J.F. 1974. Ring size in epoxynitrite cyclization. A general synthesis of functionally substituted cyclobutanes. Application to ()-grandisol. J. Am. Chem. Soc. 96:5270-5272.
Trost, B.M., and Keeley, D.E. 1975. New synthetic methods. Secoalkylative approach to grandisol. J. Org. Chem. 40:2013-2013.
Trost, B.M., Keeley, D.E., Arndt, H.C., and Bogdanowicz, M.J. 1977. New synthetic reactions. Synthesis of cyclobutanes, cyclobutenes, and cyclobutanones. Applications in geminal alkylation. J. Am. Chem. Soc. 99:3088-3100.
Tumlinson, J.H., Hardee, D.D., Gueldner, R.C., Thompson, A.C., Hedin, P.A., and Minyard, J.P. 1969. Sex pheromones produced by male boll weevil: isolation, identification, and synthesis. Science. 166:1010.
Wenkert, E., Berges, D.A., and Golob, N.F. 1978. Oxycyclopropanes in organochemical synthesis. Total syntheses of (-)-valeranone and ()-grandisol. J. Am. Chem. Soc. 100:1263-1267.
Zurflueh, R.L., Dunham, L.L., Spain, V.L., and Siddall, J.B. 1970. Synthetic studies on insect hormones. IX. Stereoselective total synthesis of a racemic boll weevil pheromone. J. Am. Chem. Soc. 92:425-427.

Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <>.
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