A new annulation method. Total syntheses of the sesquiterpenoids (+/-)-chiloscyphone and (+/-)-6-epi-chiloscyphone
The efficacy of a new annulation method, developed for the construction of functionalized bicyclic compounds, is illustrated by conversion of the β-keto esters 18 and 19 into the bicyclonon-1-enes 33 and 34, respectively, and by transformation of 2-methoxycarbonylcyclopentanone (20) into the bicyclonon-6-ene 38 and the bicyclodec-7-enes 48 and 51.Application of the method to total syntheses of the structurally unusual sesquiterpenoids (+/-)-chiloscyphone (16) and (+/-)-6-epi-chiloscyphone (17) is described.
Piers, Edward,Tse, Hoi Lun Allan
p. 983 - 994
(2007/10/02)
Convenient Synthesis of Alkyl (Z)- and (E)-2,3-Bis(trimethylstannyl)alk-2-enoates and N,N-Dimethyl (E)-2,3-Bis(trimethylstannyl)alk-2-enamides
Palladium(0)-catalysed addition of (Me3Sn)2 to the α,β-acetylenic esters (1a-n) and amides (4a-d) provides the (Z)-2,3-bis)trimethylstannyl)alk-2-enoates (2a-n) and the (E)-2,3-bis(trimethylstannyl)alk-2-enamides (6a-d), respectively; thermolysis of (2a-h
Piers, Edward,Skerlj, Renato T.
p. 626 - 627
(2007/10/02)
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