1976
DOI: 10.1002/jhet.5570130417
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis of S(+) and R(‐)‐3‐(2‐aminopropyl)indole from ethyl‐D‐ and L‐tryptophanate

Abstract: A stereospecific requirement for hallucinogenesis applies to certain molecules containing an asymmetric center. Thus, only the R‐isomers of substituted phenylisopropylamines and lysergic acid diethylamide are psychotomimetic. The enantiomers of a minor hallucinogen, S(+)‐ and R(‐)‐3‐(2‐aminopropyl)indole (α‐methyltryptamine) (6a and 6b) were synthesized via a 5‐step manipulation from D‐ and L‐tryptophan ethyl ester hydrochloride, respectively. Optical purity of these two isomers was determined by pmr spectrosc… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1

Citation Types

1
6
0

Year Published

1976
1976
2012
2012

Publication Types

Select...
7
1

Relationship

1
7

Authors

Journals

citations
Cited by 25 publications
(7 citation statements)
references
References 20 publications
1
6
0
Order By: Relevance
“…Furthermore, the stereoselectivity of AANAT could have preparative applications in the production of pharmacologically active ␣-methyltryptamine congeners (17).…”
mentioning
confidence: 99%
“…Furthermore, the stereoselectivity of AANAT could have preparative applications in the production of pharmacologically active ␣-methyltryptamine congeners (17).…”
mentioning
confidence: 99%
“…An earlier report (18) as that used previously (18). In contrast to the corresponding indole analog, the N-benzyloxycarbonyl-O-ptoluenesulfonyl intermediate (IV) is a stable, crystalline solid.…”
Section: (+)-Isomers Of Amphetamine [Dextroamphetamine (V)]mentioning
confidence: 75%
“…Analysis was carried out using the indole C-2 proton and optical rotation data were also given. The levo-rotatory isomer was found to have the same configuration as levoamphetamine (R) [51].…”
Section: Repke Reported the First Asymmetric Synthesis Of S-(+)mentioning
confidence: 94%
“…and R-(−)-AMT from ethyl d-and l-tryptophanate [51]. A five-step synthesis starting from ethyl S-tryptophanate gave R-AMT.…”
Section: Repke Reported the First Asymmetric Synthesis Of S-(+)mentioning
confidence: 99%