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Frost, C.7
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Magnus, P.9
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2. Magnus, P.; Booth, J.; Diorazio, L.; Donohoe, T. G.; Lynch, V.; Magnus, N.; Mendoza, J.; Pye, P.; Tarrant, J. G. Tetrahedron, 1996, 52, 14103.
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3
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0011984274
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note
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3 ether III, followed by butyl lithium gave IV. So at least an intramolecular addition is feasible. Deprotection of I and conversion of the C-20 alcohol into the ether V, followed by treatment with t-butyl lithium gave the carbenoid cyclopropanation adduct VI (structure by X-ray). The reluctance of the compound I to undergo addition directed our efforts towards examining a semi-pinacol-type rearrangement in the top-half of the bicyclo[5.4.0]undecenone structure. (equation presented)
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4
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0001726756
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The semipinacol and other rearrangements
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5. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
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Magnus, P.8
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5. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
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5. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
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5. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
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0011991407
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note
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14. Treatment of 50 with DBU gave a mixture which contains two unsaturated aldehydes, tentatively assigned the structures VII and VIII. The presence of VIII was indicated by a proton at δ 6.9 (dd); The formation of VIII indicates that the isomerization of the C-3/4 double bond into the C-4/5 position, as suggested in Scheme 5 is feasible, but under basic conditions no ring expansion was observed. (equation presented)
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