I. Uemura, H. Miyagawa, T. Ueno
Mar 18, 2002
Citations
0
Influential Citations
11
Citations
Journal
Tetrahedron
Abstract
Abstract A practical total synthesis of AK-toxins (AK-toxin I, 1 ; II, 2 ), host-specific toxins against the Japanese pear, has been achieved in 10% total yield, starting from the key intermediate 6 . The (2E,4Z,6E)-conjugated triene system was successfully constructed by the use of the Stille coupling reaction between the (E,Z)-bromodiene ( 17 ) and (E)-stannylacrylate ( 21 ). The (E,Z)-configuration of 17 was established with excellent geometrical purity by palladium-catalyzed stereoselective hydrogenolysis of gem-dibromide ( 15 ), which was derived from 6 via the Wittig–Horner reactions.