Synthesis of a tetrasubstituted arylphosphonate via the anionic phospho-Fries rearrangement

Tetrahedron Letters

Volumn 46, Issue 25, 2005, Pages 4311-4313

  Jayasundera, Krishanthi P ^a   Watson, Amy J ^a   Taylor, Carol M ^a  

^a MASSEY UNIVERSITY   (New Zealand)

Author keywords

Fries rearrangement; Phosphonate; Zearalenone

Indexed keywords

ANION; ESTER DERIVATIVE; ORGANOTIN COMPOUND; PHENOL; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS; STYRENE; ZEARALENONE;

ARTICLE; CATALYSIS; HYDROLYSIS; MOLECULE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 19444376123     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.104     Document Type: Article

References (15)

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6. Zearalenone was first synthesized at Merck Sharp and Dohme in Rahway: D. Taub, N.N. Girotra, R.D. Hoffsommer, C.H. Kuo, H.L. Slates, S. Weber, and N.L. Wendler Tetrahedron 24 1968 2443 2461 An extensive list of previous synthetic work is beyond the scope of this letter
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13. Use of ring-closing metathesis (RCM) as the macrocyclization step in the synthesis of zearalenone: A. Fürstner, O.R. Thiel, N. Kindler, and B. Bartkowska J. Org. Chem. 65 2000 7990 7995
14. Compound 10 has also been prepared via the monotosylate: K. Chiba, T. Arakawa, and M. Tada J. Chem. Soc., Perkin Trans. 1 1998 2939 2942
15. These values were obtained from SciFinder Scholar, which states that they were calculated using Advanced Chemistry Development (ACD/Labs) Software Solaris V4.67, error: ±0.2 units