Issue 2, 1998
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Novel squalestatin derivatives arising from reactions at the allylic centre of the C1-side chain

Panayiotis A. Procopiou,   Brian W. Dymock,   Graham G. A. Inglis,   Michael G. Lester,   Andrew D. Roberts,   Philip J. Sidebottom,   Stephen J. Spooner,   Anton R. P. Srikantha  and  Nigel S. Watson  

Abstract

Reaction of 2 with Ac2O–TMSOTf gives the triacetate 5, which on further reaction gives isomer 6, arising from an allylic rearrangement, whereas reaction of 2 with Et3SiH–TMSOTf gives tricycle 7 arising from addition of the C7-OH to the allylic centre. Attempted ionic reduction of triacetate 5 gives benzocycloheptene 8, arising from Friedel-Crafts alkylation of the phenyl ring by the allylic centre. Similar alkylation has been obtained with analogue 9, and with the trifluoromethanesulfonate ester of the allylic alcohol 13. Attempted ionic reduction of 17, lacking the allylic centre, gives 20 arising from ester hydrolysis at C4.

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Article information

DOI
https://doi.org/10.1039/A704363E
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1998, 327-334

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Novel squalestatin derivatives arising from reactions at the allylic centre of the C1-side chain

P. A. Procopiou, B. W. Dymock, G. G. A. Inglis, M. G. Lester, A. D. Roberts, P. J. Sidebottom, S. J. Spooner, A. R. P. Srikantha and N. S. Watson, J. Chem. Soc., Perkin Trans. 1, 1998, 327 DOI: 10.1039/A704363E

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