10285-06-0Relevant articles and documents
Enantiospecific synthesis of (+)- and (-)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine
Nambu, Mitch,White, James D.
, p. 1619 - 1620 (1996)
Asymmetric dihydroxylation of (E)-ethyl 2-isopropylbut-2-enoate with AD-mix-a and AD-mix-P, followed by saponification, gives (-)- and (+)-trachelanthic acids, respectively, which are each coupled via their acetonides with (+)-retronecine to yield the pyrrolizidine alkaloids indicine and intermedine.
Total syntheses of indicine N-oxide, intermedine N-oxide, and their enantiomers using carbohydrate as a chiral educt
Nishimura,Kondo,Takeuchi,Umezawa
, p. 4107 - 4113 (2007/10/02)
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Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents
Zalkow,Glinski,Gelbaum,Fleischmann,McGowan,Gordon
, p. 687 - 694 (2007/10/02)
(-)- and (+)-trachelanthic and (-)- and (+)-viridifloric acids were synthesized and their isopropylidene derivatives were regiospecifically coupled, at C-9, with (-)-retronecine (2) obtained by hydrolysis of monocrotaline (1), isolated from Crotalaria spectabilis. Hydrolysis, followed by oxidation, led to the N-oxides of indicine (7), intermedine (13), lycopsamine (15), and the new nonnatural product 16, respectively. Each of these analogues was screened in the P388 lymphocytic leukemia system at the same time as indicine N-oxide, and the results were compared. Other related analogues were prepared and similarly screened and the results compared with those from indicine N-oxide.
