67209-77-2Relevant academic research and scientific papers
Formal total synthesis of (±)-trichodiene via Claisen rearrangement and Robinson annulation
Jung, Jae-Chul,Jung, Young-Jo,Park, Oee-Sook
experimental part, p. 293 - 297 (2009/01/31)
A facile formal total synthesis of (±)-trichodiene was achieved by employing Claisen rearrangement and Robinson annulation as synthetic key strategies.
Asymmetric synthesis of (-)-trichodiene. Generation of vicinal stereogenic quaternary centers via the thio-Claisen rearrangement
Lemieux, René M.,Meyers
, p. 5453 - 5457 (2007/10/03)
The use of chiral bicyclic lactams, in their thiocarbonyl form 9, has been shown to serve as important intermediates for producing α-quaternary alkyl derivatives 8, which were readily transformed into the title compound (-)-1. The reversibility of the thi
Stereoselective construction of the dicyelopenta[a,d]cyclooctene core of the ceroplastin sesterterpenes by way of the anionic oxy-cope rearrangement
Paquette, Leo A.,Liang, Shaowo,Wang, Hui-Ling
, p. 3268 - 3279 (2007/10/03)
Bicyclo[3.2.1]oetanediones such as 9, which are readily available by double carbonylation of (1,3-cyclohexadiene)iron tricarbonyl complexes according to Eilbracht, are amenable to regiospecific methylenation under Wittig conditions. Reduction of 10 with copper hydride leads to 11, which can be resolved by application of Johnson's sulfoximine technology and oxidized to give the enantiopure antipodes of 10. Variously substituted cyclopentenyl anions undergo 1,2-addition to 10, providing carbinols which are capable of anionic oxy-Cope rearrangement via chair transition states. These structural reorganizations are fully stereocontrolled and lead directly to functionalized dicyclopenta[a,d]cyclooctenes. When 11 is treated analogously, only [1,3] sigmatropy is observed and inversion of stereochemistry at the migrating carbon prevails. Both processes exhibit impressive scaffolding powers and are characterized by brevity.
Studies in Cephalotaxus Alkaloids. Stereospecific Total Synthesis of Homoharringtonine
Hiranuma, Sayoko,Shibata, Misako,Hudlicky, Tomas
, p. 5321 - 5326 (2007/10/02)
The alkaloid ester homoharringtonine (2) was synthesized stereospecifically via the Reformatsky reaction of methyl α-bromoacetate with cephalotaxyl pyruvate (16) obtained by esterification of cephalotaxine with acid chloride derived from 15.The preparations of 2 and its unsaturated derivative 13 are described in detail.Possible explanations of the steric requirements in the esterification of cephalotaxine and of the steric outcome of the Reformatsky reaction leading to 2 and 13 are advanced.
α-OXOKETENE DITHIOACETALS: VERSATILE SUBSTRATES FOR 1,3-CARBONYL TRANSPOSITIONS
Dieter, R. Karl,Jenkitkasemwong, Yawares
, p. 3747 - 3750 (2007/10/02)
A two step procedure for the conversion of α-oxoketene dithioacetals to β-substituted α,β-unsaturated thioesters or acids is described.The overall transformation represents a 1,3-carbonyl transposition in which the original ketone carbonyl emerges as the carbonyl of an acid or thioester.The resulting thioesters and acids constitute versatile acylating reagents in accord with established procedures.
