Total syntheses of the strobilurins G, M, and N

The key reactions in the general synthesis of strobilurins are the highly ( Z)-selective Wittig reaction of an ( E)-cinnamaldehyde with the phosphorus ylide 8 derived from (1,1-dibromoethyl)triphenylphosphonium bromide, followed by bromine–iodine exchange and Pd–Cu co-catalyzed Stille cross-coupling...

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Bibliographic Details
Published in:Tetrahedron 2004-05, Vol.60 (22), p.4921-4929
Main Authors: Kroiß, Stefan, Steglich, Wolfgang
Format: Article
Language:English
Subjects:
Benzodioxepins
Fungicides
Natural products
Strobilurins
Total synthesis
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Summary:The key reactions in the general synthesis of strobilurins are the highly ( Z)-selective Wittig reaction of an ( E)-cinnamaldehyde with the phosphorus ylide 8 derived from (1,1-dibromoethyl)triphenylphosphonium bromide, followed by bromine–iodine exchange and Pd–Cu co-catalyzed Stille cross-coupling of the resulting alkenyl iodide with methyl ( Z)-2-tributylstannyl-3-methoxyacrylate ( 7 ). The synthetic strobilurins G, M, and N were identical with the corresponding natural compounds. In addition, the (2′ S)-configuration of strobilurin G ( 1 ) was unambiguously established by oxidative degradation of the synthetic intermediate ( S)- 9 to ( R)-2,3-dihydroxyisovaleric acid. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.03.092