479636-99-2Relevant articles and documents
Synthetic studies of kampanols, novel p21ras farnesyltransferase inhibitors: An efficient synthesis of the tetracyclic ABCD ring system of kampanols
Iwasaki, Katsuhiko,Nakatani, Mari,Inoue, Munenori,Katoh, Tadashi
, p. 8763 - 8773 (2007/10/03)
An enantioselective synthesis of the tetracyclic ABCD ring system (4) of kampanols, novel Ras farnesyltransferase inhibitors from a microorganism, was efficiently achieved for the first time starting from the known trans-decalone derivative 9. The synthetic method involves the following two key steps: (i) a conjugate addition reaction between the α-methylene ketone 6 and the Grignard reagent (7) of the ortho-disubstituted bromobenzene derivative 8 to deliver the coupling product 21 with stereoselectivity at the C9 position and (ii) a phenylselenium-mediated cyclization reaction of the phenol derivative 5 to stereoselectively construct the requisite tetracyclic intermediate 25 possessing the cis-fused connectivity of the B/C rings.
Studies toward the total synthesis of (-)-kampanol A: An efficient construction of the ABCD ring system
Iwasaki, Katsuhiko,Nakatani, Mari,Inoue, Munenori,Katoh, Tadashi
, p. 7937 - 7940 (2007/10/03)
The optically active tetracyclic ABCD ring system 2 of (-)-kampanol A (1), a novel Ras farnesyltransferase inhibitor from a microorganism, was efficiently synthesized starting from the known ketol 4 as a model study. The synthetic method involves conjugate addition reaction of the Grignard reagent of the bromobenzene derivative 14 to the α-methylene ketone 10 to form the coupling product 15 and phenylselenium-mediated cyclization reaction of the phenol derivative 17 to stereoselectively construct the requisite tetracyclic intermediate 18 as the pivotal steps.
