84094-71-3

Upstream product

• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 100-52-7 benzaldehyde 
• 153-94-6 D-tryptophan 
• 4299-70-1 D-Tryptophan methyl ester 

Downstream Products

• 84094-72-4 (1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid 
• 84094-73-5 (1R,3R)-(-)-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid 
• 84129-58-8 trans-(1S,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate 
• 84129-59-9 cis-(1R,3R)-(+)-methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-6-oxocanthine-2-carboxylate 
• 185419-04-9 (1R,3R)-2-Benzyl-1-[1,3]dithian-2-ylmethyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 84094-74-6 (1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 197143-13-8 (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole 
• 217448-24-3 (6S,10S)-(-)-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole 
• 913556-71-5 C₂₈H₂₆N₂O₂S 
• 1355163-06-2 (R,E)-methyl-5-((3-(1H-indol-3-yl)-1-methoxy-1-oxo-propan-2-yl)(benzyl)amino)-3-oxopent-4-enoate 
• 1355163-11-9 C₂₁H₂₂N₂O₂ 
• 84094-75-7 cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 245760-13-8 C₂₉H₃₆N₂O₄ 
• 245760-13-8 C₂₉H₃₆N₂O₄ 

Relevant academic research and scientific papers

The enantiospecific total synthesis of norsuaveoline

Norsuaveoline la has been synthesized enantiospecifically in 28% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled oxy-anion Cope rearrangement as key steps.

Biology-oriented combined solid-and solution- phase synthesis of a macroline-like compound collection

Macrolines constitute a class of natural products that has more than 100 members and displays diverse biological activities. These compounds feature a cycloocta[b]indole scaffold that represents an interesting target structure for biology-oriented synthesis (BIOS). We have presented a solid-phase synthesis of isomerically pure cycloocta[b]indoles by employing the Pictet-Spengler reaction and the Dieckmann cyclization as key steps. The scope of this reaction sequence was investigated in more detail by using various additional diversification procedures, such as Pd-catalyzed Sonogashira or Suzuki couplings on a solid phase, thus allowing, for example, the generation of 10-substituted cycloocta-[b]indole derivatives. Finally, solution-phase decoration of the cycloocta[b]indole skeleton by reduction and saponification was evaluated, thereby further extending the scope of the solid-phase synthesis.

General approach for the synthesis of sarpagine indole alkaloids. Enantiospecific total synthesis of (+)-vellosimine, (+)-normacusine B, (-)-alkaloid Q3, (-)-panarine, (+)-Na-methylvellosimine, and (+)-Na-methyl-16-epipericyclivine

The first total synthesis of (+)-Na-methyl-16-epipericyclivine (9) was completed [from D-(+)-tryptophan methyl ester] in an overall yield of 42% (eight reaction vessels). The optical rotation [[α]D +22.8 (c 0.50, CHCl3)] obtained on this material confirmed that the reported optical rotation [[α]D 0 (c 0.50, CHCl 3)]47 was biogenetically unreasonable. The total syntheses of (+)-vellosimine, (+)-normacusine B, (-)-alkaloid Q3, (-)-panarine, and (+)-Na-methylvellosimine are also described. Moreover, a mixed sample (1:1) of synthetic (-)-panarine and natural (-)-panarine yielded only one set of signals in the 13C NMR; this indicated that the two compounds are identical and further confirmed the correct configuration of (+)-vellosimine, (+)-normacusine B, and (-)-alkaloid Q3. In this approach, the key templates, (-)-Na-H,N b-benzyltetracyclic ketone 15a and (-)-Na-methyl,N b-benzyltetracyclic ketone 43 were synthesized on multihundred gram scale by the asymmetric Pictet-Spengler reaction and a stereocontrolled Dieckmann cyclization via improved sequences. An intramolecular palladium (enolate-mediated) coupling reaction was employed to introduce the C(19)-C(20) E-ethylidene function in the sarpagine alkaloids for the first time in stereospecific fashion.

Enantiospecific Total Synthesis of the Sarpagine Related Indole Alkaloids Talpinine and Talcarpine as Well as the Improved Total Synthesis of Alstonerine and Anhydromacrosalhine-methine via the Asymmetric Pictet-Spengler Reaction

The enantiospecific total synthesis of talpinine 1 and talcarpine 2 has been accomplished from D-(+)-tryptophan in 13 steps (11 reaction vessels) in 10% and 9.5% overall yields, respectively. Moreover, this synthetic approach has been employed for the improved synthesis of alstonerine 3 and anhydromacrosalhine-methine 4 in 12% and 14% overall yield, respectively. A convenient synthetic route for the enantiospecific, stereospecific preparation of the key intermediate (-)-Na-H, Nb-benzyl tetracyclic ketone 15a via the asymmetric Pictet-Spengler reaction on a multihundredgram scale has been developed. A diastereocontrolled (>30:1) anionic oxy-Cope rearrangement and the intramolecular rearrangement to form ring-E and an Nb-benzyl/Nb-methyl transfer reaction also served as key steps. This general approach can now be utilized for the synthesis of macroline/ sarpagine related indole alkaloids and their antipodes for biological screening.

General approach for the synthesis of ajmaline/sarpagine indole alkaloids: Enantiospecific total synthesis of (+)-ajmaline, alkaloid G, and norsuaveoline via the asymmetric Pictet-Spengler reaction

A general approach (oxyanion-Cope strategy) for the synthesis of sarpagine/ajmaline indole alkaloids has been developed. (+)-Ajmaline 1 and alkaloid G 2 as well as norsuaveoline 3 have been synthesized from D-(+)-tryptophan in enantiospecific fashion via