480-87-5Relevant articles and documents
Synthesis and Stereochemistry of Dicrotaline, a Macrocyclic Pyrrolizidine Alkaloid
Devlin, J. Alastair,Robins, David J.
, p. 1272 - 1274 (1981)
Dicrotaline (3) and its C-13 epimer (4) have been synthesized and the absolute configuration at C-13 of both alkaloids has been established by specific degradation of each epimer to optically active mevalonolactone.
A Tin-Mediated One-Step Synthesis of (+)-Dicrotaline, an 11-Membered Dilactonic Pyrrolizidine Alkaloid
Niwa, Haruki,Okamoto, Osamu,Ishiwata, Hiroyuki,Kuroda, Akio,Uosaki, Youichi,Yamada, Kiyoyuki
, p. 3017 - 3019 (2007/10/02)
A new synthesis of (+)-dicrotaline (1), an 11-membered dilactonic pyrrolizidine alkaloid of retronecine (6) type has been achieved in one step by utilizing a tin-mediated lactonization process.
Macrocyclic Pyrrolizidine Alkaloids. Synthesis and Stereochemistry of (+)-Dicrotaline (13β-Hydroxy-13α-methyl-1,2-didehydrocrotalanine) and (+)-13-epi-Dicrotaline
Brown, Kenneth,Devlin, J. Alastair,Robins, David J.
, p. 1819 - 1824 (2007/10/02)
Treatment of (+)-retronecine (1) with the trimethylsilyl ether of 3-hydroxy-3-methylglutaric anhydride gave a mixture of the 7- and 9-monoesters of (+)-retronecine (1).Lactonisation of this mixture was achieved using the corresponding pyridine-2-thiol esters to give (+)-dicrotaline (13β-hydroxy-13α-methyl-1,2-didehydrocrotalanine) (2) and (+)-13-epi-dicrotaline (3).The absolute configuration at C-13 in both compounds was established by a sequence of selective reactions on each epimer to yield optically active mevalonolactone.
