Total synthesis of (±)-heliannuol D, an allelochemical from Helianthus annuus

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1151-1154

  Vyvyan, James R ^a   Looper, Ryan E ^a  

^a WESTERN WASHINGTON UNIVERSITY   (United States)

Author keywords

Allelopathy; Biomimetic reactions; Herbicides; Phenols

Indexed keywords

ANISOLE DERIVATIVE; BENZOXEPIN DERIVATIVE; EPOXIDE; HELIANNUOL D; HERBICIDE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SUNFLOWER; SYNTHESIS;

EID: 0034685210     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02284-4     Document Type: Article

References (31)

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24. This somewhat disappointing yield for the coupling and reduction sequence is in stark contrast to similar coupling reactions of aryl zinc species with the same vinyl triflate that proceed in 85-90% yield for the 2 step sequence: Looper, R. E. M. S. Thesis, Western Washington University: Bellingham, WA, 1999.
25. 10=2.83, dd, J=9 and 3 Hz; The stereochemical assignment was confirmed by X-ray diffraction of a model 2-(5-methyl-2H,3H,4H,5H-benzo[f]oxepan-2-yl)propan-2-ol. Details of the stereochemical correlation will be reported in the full article describing this work.
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27. For some relevant phenol-epoxide cyclizations, see: (a) Arnone, A.; Bernardi, R.; Bravo, P.; Frigerio, M.; Ticozzi, C. Gazz. Chim. Ital. 1989, 119, 87-94 and references cited therein. (b) Krohn, K.; Baltus, W. Tetrahedron 1988, 44, 49-54. (c) Weerawarna, S. A.; Guha-Biswas, M.; Nelson, W. L. J. Heterocycl. Chem 1991, 28, 1395-1403.
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31. The melting point of our synthetic 4 is 162-163°C, 100 degrees higher than was reported for the natural material in the original work (Ref 7b). Professor Macías confirmed via personal communication that an error exists in the original paper, and that the melting point of natural heliannuol D is 159-161°C.