5523-37-5Relevant academic research and scientific papers
Bacterial biotransformation of 3α(S)-strictosidine to the monoterpenoid indole alkaloid vallesiachotamine
Shen, Zhengwu,Eisenreich, Wolfgang,Kutchan, Toni M.
, p. 293 - 296 (2007/10/03)
3α(S)-Strictosidine produced by heterologously expressed strictosidme synthase from Rauwolfia serpentina was used in biotransformation experiments with a series of 22 bacterial strains.All strains tested were found to deglucosylate and rearrange the alkaloid to vallesiachotamine, thereby providing an example of how gene technology and microbial biotransformation can be combined for the biotechnological production of alkaloidal natural products. - Keywords: Rauwolfia serpentina, Spodoptera frugiperda, baculovirus, strictosidine synthase, vallesiachotamine.
Reaction of chiral nucleophiles with pyridinium compounds. Total synthesis of the indole alkaloids (-)-isovallesiachotamine and (+)-vallesiachotamine
Amann, Robert,Arnold, Karen,Spitzner, Dietrich,Majer, Zsuzsanna,Snatzke, Guenther
, p. 349 - 355 (2007/10/03)
The addition of the chiral nucleophiles Na-2 and Li-5 to pyridinium compounds 1 and the subsequent ring closure (Pictet-Spengler cyclization) to indoloquinolizines 3a and 7b, respectively, proceed stereoselectively (d.e. for 3a: 54%; for 7b: ≥95 %). Proof for the absolute configuration of these products is provided by their CD spectral data and the transformation of 7b into the indole alkaloids (+)-vallesiachotamine [(Z)-6] and (-)-isovallesiachotamine [(E)-6]. VCH Verlagsgesellschaft mbH, 1996.
Synthesis of Vallesiachotamine
Spitzner, Dietrich,Zaubitzer, Thomas,Shi, Yau-Jun,Wenkert, Ernest
, p. 2274 - 2278 (2007/10/02)
Interaction of methyl N-tryptophylnicotinate bromide with the lithium salt of ethyl α-(trimethylsilyl)acetate and acid-catalyzed cyclization has yielded a tetracyclic ester, whose condensation with acetaldehyde has produced ethyl vallesiachotamate.Reactions of lithiated, alkylthiolated esters with the nicotinate salt (followed by cyclization) have afforded related adducts.Ester-to-aldehyde group conversion has to the alkaloid vallesiachotamine in the 19Z and 19E forms.
