Crystal Structure of Akuammigine Picrate Hydrate

Abstract

The single-crystal X-ray data of akuammigine picrate hydrate (1 · Picr · H 2 O) confirm the relative configuration of the indole alkaloid akuammigine (1) as epiallo (Fig.

Tetrahydroalstonine

“…For the biological activity of TMA, see Zou et al (2010); Sharma et al (1988). For a related structure, see: Laus & Wurst (2008).…”

“…The structure of THA has been elucidated after extensive NMR studies during the period 1950-1960 (Wenkert & Roychaudhuri 1957;Wenkert et al 1961). In the corynanthe series, only the crystal structure of akuammigine (as picrate hydrate) has been previously reported (Laus & Wurst 2008). There have been only a few reports of the THA biological activities (Zou et al 2010;Sharma et al 1988).…”

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

“…Compounds 173 and 175 were tested for antimalarial, antitrypanosomal and cytotoxic activity. 76 The methanol extract from stems of Conchocarpus gaudichaudianus yielded three new indole alkaloids, 3- (178). 77 Six new alkaloids, notoamides F (179), G (180), H (181), I (182), J (183) and K (184), have been isolated from a marinederived Aspergillus sp., and their absolute configurations were elucidated.…”

“…The single-crystal X-ray data of akuammigine picrate hydrate confirmed the relative configuration. 178 A total synthesis of (AE)-yohimbenone (439) has been achieved through a conjugate addition-dipolar cycloaddition of 2,3bis(phenylsulfonyl)-1,3-butadiene (440) with oxime as the key step (Scheme 77). 179 A enantioselective formal synthesis of (+)-dihycorynantheine (441) and (À)-dihydrocorynantheol (442) has been accomplished by the synthesis of a known synthetic precursor through a stereoselective cyclocondensation of (S)-tryptophanol with a racemic aldehyde and a stereoselective cyclization of the lactam (Scheme 78).…”

Asymmetric Diels–Alder Reaction of 3-Vinylindoles and Nitroolefins Promoted by Multiple Hydrogen Bonds

“…1-Amino-hydrocarbazole is an important structural unit frequently found in the akuammiline alkaloids. 1 Examples include aspidophylline A, 2 lonicerine, 3 picrinine, 4 aspidodasycarpine, 5 strictamine, 1a scholarisine, 6 cathafoline, 2c lanciferine, 7 and akuammigine 8 (Figure 1). As many akuammiline alkaloids exhibit exciting biological activities, 9 the preparation of chiral 1-aminohydrocarbazole derivatives has attracted interest for the discovery of akuammiline analogues with potentially good biological profiles.…”