172959-08-9Relevant academic research and scientific papers
Syntheses of two possible diastereoisomers of the epoxy lactone proposed for an annonaceous acetogenin, epoxyrollin A
Konno, Hiroyuki,Makabe, Hidefumi,Tanaka, Akira,Oritani, Takayuki
, p. 9399 - 9408 (2007/10/03)
Syntheses of two possible diastereoisomers (5S, 18'S, 19'R)- and (5S, 18'R, 19'S)-1 corresponding to the epoxy lactone that has been proposed for epoxyrollin A, a structural representative of biosynthetic precursors of tetrahydrofuran annonaceous acetogenins, are described. The 13C-NMR and tandem mass spectral data of the synthetic samples were not in accord with those recorded for natural epoxyrollin A. Consequently, the structure of epoxyrollin A needs to be revised.
Synthesis of Two Possible Diastereoisomers of the Epoxy Lactone Proposed for Epoxyrollin A
Konno, Hiroyuki,Makabe, Hidefumi,Tanaka, Akira,Oritani, Takayuki
, p. 2355 - 2357 (2007/10/03)
Syntheses of two possible stereoisomeric epoxy lactones (20S,21R)- and (20R,21S)-1 that have been proposed for epoxyrollin A, a structural representative of biosynthetic precursors of tetrahydrofuran annonaceous acetogenins, are described.Protected dihydroxy compound 4, which is the latent epoxy moiety of (20S,21R)- and (20R,21S)-1, was prepared by an 8-step sequence via Sharpless asymmetric dihydroxylation, starting from allyl alcohol 6.Preparation of γ-lactone moiety 5 was conducted by the method reported earlier.A palladium-catalyzed cross coupling reaction of 4 with 5 gave enyne 3, which, by a 3-step sequence, was converted into (20S,21R)-and (20R,21S)-1.The 13C-NMR and mass spectral data of the two synthetic diastereoisomers are not in accordance with those recorded for epoxyrollin A.Consequently, the structure of epoxyrollin A needs to be revised.
