The synthesis of the C6-C14 fragment of euphosalicin, a highly oxygenated modified jatrophane diterpene, is described. Key steps in the preparation of this versatile intermediate are an Ireland-Claisen rearrangement and a Shibasaki direct asymmetric aldol reaction.
Synthesis of the proposed structure of feigrisolide C
(Chemical Equation Presented) Possible structures of feigrisolide C were synthesized via ring-closing olefin metathesis reaction of a diester derivative prepared from 8-epinonactic acid, but physical characteristics of the synthetic samples did not match with those of the natural sample of feigrisolide C.
Woo, Han Kim,Jae, Hoon Jung,Lee, Taek Sung,Sang, Min Lim,Lee, Eun
p. 1085 - 1087
(2007/10/03)
1,4- and 1,5-Stereoselection by Sequential Aldol Addition to α,β-Unsaturated Aldehydes Followed by Claisen Rearrangement. Application to Total Synthesis of the Vitamin E Side Chain and the Archaebacterial C40 Diol
A synthetic strategy has been developed wherein the high 1,2-stereoselection obtainable from aldol reaction of an α,β-unsaturated aldehyde is parlayed by a subsequent Claisen rearrangement into 1,4- or 1,5-stereoselection.For example, diol monoethers 26 a
Heathcock, Clayton H.,Finkelstein, Bruce L.,Jarvi, Esa T.,Radel, Peggy A.,Hadley, Cheri H.
p. 1922 - 1942
(2007/10/02)
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