Synthesis of nemorosone via a difficult bridgehead substitution reaction

Synlett

Volumn , Issue 4, 2010, Pages 639-643

  Simpkins, Nigel S ^a   Taylor, James D ^a   Weller, Michael D ^a   Hayes, Christopher J ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

B3LYP calculations; Bridgehead substitution; Iodine lithium exchange; Nemorosone

Indexed keywords

IODINE; LITHIUM; NEMOROSONE; PHLOROGLUCINOL DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CALCULATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; IODINATION; MOLECULAR MODEL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 77955441739     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219371     Document Type: Article

References (26)

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21. 1H NMR
22. 3, making these the solvents of choice for NMR work.
23. Our synthesis is about the same length as the Danishefsky route and proceeds in similarly modest overall yield of about 1-2%.
24. +: 511.3220; found: 511.3228.
25. Hayes, C. J.; Simpkins, N. S.; Kirk, D. T.; Mitchell, L.; Baudoux, J.; Blake, A. J.; Wilson, C. J Am. Chem. Soc. 2009, 131, 8196.
26. * level of theory using Spartan 04 (Windows), and zero-point vibrational energies were calculated for all structures, and the absence of imaginary frequencies was used to characterise the structures as minima on their potential energy surfaces. NBO calculations were performed on all anionic species using the NBO keyword in Spartan 04 (Windows): Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, D.; Adamson, R. D.; Furlani, T. R.; Lee, M. S.; Lee, A. M.; Gwaltney, S. R.; Adams, T. R.; Ochsenfeld, C.; Gilbert, A. T. B.; Kedziora, G. S.; Rassolov, V. A.; Maurice, D. R.; Nair, N.; Shao, Y.; Besley, N. A.; Maslen, P. E.; Dombroski, J. P.; Daschel, H.; Zhang, W.; Korambath, P. P.; Baker, J.; Byrd, E. F. C.; Van Voorhis, T.; Oumi, M.; Hirata, S.; Hsu, C.-P.; Ishikawa, N.; Florian, J.; Warshel, A.; Johnson, B. G.; Gill, P. M. W.; Head-Gordon, M.; Pople, J. A. J Comput. Chem. 2000, 21, 1532.