Enantioselective total synthesis of cyathin A3

Organic Letters

Volumn 9, Issue 15, 2007, Pages 2843-2846

  Ward, Dale E ^a   Shen, Jianheng ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYATHINS; DITERPENE; UNCLASSIFIED DRUG;

ARTICLE; HYDROGEN BOND; STEREOISOMERISM; SYNTHESIS;

DITERPENES; HYDROGEN BONDING; STEREOISOMERISM;

EID: 34547207608     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070994z     Document Type: Article

References (65)

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50. This problem was solved by using 3-iodo-2,5-dimethylbenzoquinone (ref 16a).; however, the regioselectiviy obtained with unsymmetrical dienes is opposite to our requirements
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53. The structure of Mikami's catalyst is unknown. For a review of Ti(IV)-based enantioselective catalysts, see: Ramon, D. J.; Yus, M. Chem. Rev. 2006, 106, 2126-2208.
54. Control experiments showed that the reaction was strongly inhibited by the presence of 2,4-pentandione or the corresponding TMS enol ether (i.e., putative byproducts from decomposition of 13).
55. 2O.
56. 2 may preferentially absorb diene decomposition products (ref 21) or improve catalyst performance by immobilization; for example, see: Coperet, C.; Chabanas, M.; Saint-Arroman, R. P.; Basset, J.-M. Angew. Chem., Int. Ed. 2003, 42, 156-181.
57. The face designation is according to the carbon adjacent to the activated carbonyl.
58. 1 is OMe (e.g., ref 14c), presumably because coordination of 21 to the more basic carbonyl is not sufficiently activating. Because the presence of the potentially coordinating OMe group does not alter the sense of enantioselectivity, activation without chelation is implied. For related examples with other catalysts, see refs 14a,e,f.
59. In 19-catalyzed DA reactions of 12 with unsymmetrical dienes, poor regioselelctivity results from selective addition to both the syn and anti alkenes giving regioisomeric adducts each with high ee (ref 16a).
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64. (b) Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1985, 26, 1109-1112.
65. Cyathins 3 and 6 are available more directly from (-)-18 (ref 5).