A novel, highly selective, and general methodology for the synthesis of 1,5-diene-containing oligoisoprenoids of all possible geometrical combinations exemplified by an iterative and convergent synthesis of coenzyme Q10

Organic Letters

Volumn 4, Issue 2, 2002, Pages 261-264

  Negishi, Ei Ichi ^a   Liou, Show Yee ^a   Xu, Caiding ^a   Huo, Shouquan ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; POLYENE; TERPENE; UBIQUINONE; ZIRCONIUM;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; POLYENES; STEREOISOMERISM; TERPENES; UBIQUINONE; ZIRCONIUM;

EID: 0037165389     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010263d     Document Type: Article

References (35)

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2. The "head-to-tail" (H-to-T) and "tail-to-head" (T-to-H) directions in isoprenoids are defined as shown below, for the sake of convenience. Chemical equation presented.
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34. For some of the earlier applications, see (a) Whitesell, J. K.; Fisher, M.; Jardine, P. D. S. J. Org. Chem. 1983, 48, 1556. (b) McMurry, J. E.; Bosch, G. K. J. Org. Chem. 1987, 52, 4885. (c) Asao, K.; Iio, H.; Tokoroyama, T. Tetrahedron Lett. 1989, 30, 6401.
35. Although still unclear, a chelation effect due to the δ-I atom in a putative oxidation addition product may be responsible for the observed difference.