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For synthetic approaches to olivin and olivomycin A, see Datta, S.C.; Franck, R.W.; Noire, P.D. J. Org. Chem. 1984, 49, 2785; Roush, W.R.; Michaelides, M.R.; Tai, D.F.; Lesur, B.M.; Chong, W.K.M.; Harris, D.J. J. Am. Chem. Soc. 1989, 111, 2984; Sebesta, D.P.; Roush, W.R. J. Org. Chem. 1992, 57, 4799; Toshima, K.; Nozaki, Y.; Nakata, M.; Tatsuta, K.; Kinoshita, M. Tetrahedron Lett. 1993, 34, 5761; Roush, W.R.; Lin, X.-F. Tetrahedron Lett. 1993, 34, 6829; and references cited therein.
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1-Bromoprop-1-ene (Aldrich; mixture of isomers) was used as supplied. Thermal electrocyclic ring-opening of any (Z)-3,6-dimethoxy-1-(1-propenyl)benzocyclobuten-1-ol (i.e. the Z-isomer of 9e) produced in the Grignard addition step would probably be followed by the 1,7-shift of an allylic hydrogen rather than the 6π electrocyclisation (see reference 8a).
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Benzocyclobutenylmethyl systems readily undergo ring fission (or expansion) under the influence of developing negative (or positive) charge at the alpha-position (see Kündig, E.P.; Perret, C. Helv. Chim. Acta 1981, 64, 2606, and references cited therein).
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The stability of a 1-substituted-2-cyclobutene is lowered by conjugating groups at C-1 or C-4, whether electron donors or acceptors. For a discussion, see Spellmeyer, D.C.; Houk, K.N.; Rondan, N.G.; Miller, R.D.; Franz, L.; Fickes, G.N. J. Am. Chem. Soc. 1989, 111, 5356.
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For discussion, see Binns, F.; Hayes, R.; Ingham, S.; Saengchantara, S.T.; Turner, R.W.; Wallace, T.W. Tetrahedron 1992, 48, 515; Jefford, C.W.; Bernardinelli, G.; Wang, Y.; Spellmeyer, D.C.; Buda, A.; Houk, K.N. J. Am. Chem. Soc. 1992, 114, 1157; Niwayama, S.; Wang, Y.; Houk, K.N. Tetrahedron Lett. 1995, 36, 6201, and references cited therein.
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For discussion and related processes, see Stone, G.B.; Liebeskind, L.S. J. Org. Chem. 1990, 55, 4614; Wagner, P.J.; Park, B.-S.; Sobczak, M.; Frey, J.; Rappoport, Z. J. Am. Chem. Soc. 1995, 117, 7619, and references cited therein.
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(1973)
Org. Synth.
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Logullo, F.M.1
Seitz, A.H.2
Friedman, L.3
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