Biochemical Targets of Plant Bioactive Compounds by Gideon Polya

By Gideon Polya

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Chiu. M. 1] oxabicyclic substrate 82 [89]. However, the thiol nucleophile underwent both S~2 and S~q2"addition to give a 2" 1 mixture of 213 and 214, Eq. 129. 3 Sil~l Lewis Acids Mann observed a regioselective ring opening of oxabicyclic substrate 215 using TMSI in his studies directed toward the synthesis of pseudoguaianolides [ 187 a]. The regioselectivity was explained by a directed activation involving simultaneous complexation of the ester and bridging oxygen by the TMS cation. Treatment of 216 with DBU resulted in elimination to give 217 in an overall yield of 65 %,Eq.

5 h 79% yield H 222 (134) 223 It follows that the corresponding enol ethers can be ring-opened by' treatment with Lewis acid [190]. Simpkins subjected the enantiomerically enriched silyl enol ether 224 (obtained by' deprotonation using a homochiral lithium amide) to titanium tetrachloride [121]. Alkene 224 was obtained in 88 % ee at -95 ~ and the ring opened product is expected to be of comparable enantiomeric purity, Eq. 135. 0 O OTMS 224 - TiCI4, CH2CI2,-78~ 76% yield = ~ O H (135) E Chiu. M.

Reactions of ethylenic bridged oxabicyclic ketones also undergo e x o attack by organolithium reagents [105], Grignard reagents [106], dichloroketene [107] and hydridic reductions including LiA1H4 [ 108], NaBH4 [ 101,109a] and aluminum isopropoxide [ 108 ]. In an analogous fashion, enolates of ethylenic bridged ketones such as 86 are trapped predominantly from the e x o face by methyl iodide, Eq. 65 [95, 109]. In this case, the methylated ketone was subsequently reduced from the e n d o face due to the hindrance of the e x o substituent impeding the usual approach s y n to the bridgehead oxygen.

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