Sarpagin, ein neues Alkaloid aus Rauwolfia serpentina Benth
TL;DR: In this article, die Isolierung eines neuen Alkaloids aus Rauwolfia serpentina Benth is discussed, i.e., a basischen basische alkaloid, which besitzt die Bruttoformel C19H22O2N2, HX.
Abstract: Es wird die Isolierung eines neuen Alkaloids aus Rauwolfia serpentina Benth. beschrieben. Das schwach basische Alkaloid, das mit Sarpagin bezeichnet wurde, besitzt die Bruttoformel C19H22O2N2 und bildet mit Sauren bestandige kristallisierte Salze von der Zusammensetzung C19H22O2N2, HX.
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TL;DR: A concise preparation of optically active l or d-6-methoxytryptophan ethyl ester 21 was developed via the Fischer indole/Schollkopf protocol from 6-Methoxy-3-methylindole 16 (four steps, 58% overall yield).
Abstract: A concise preparation of optically active l or d-6-methoxytryptophan ethyl ester 21 was developed via the Fischer indole/Schollkopf protocol from 6-methoxy-3-methylindole 16 (four steps, 58% overall yield). This method was extended to the enantiospecific total synthesis of tryprostatin A (11) via a regiospecific bromination process as a key step. In addition, 6-methoxy-2-bromotryptophan ethyl ester (32), a potential intermediate for indole alkaloid synthesis, was prepared via this strategy.
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TL;DR: Alkaloids 1 and 2 are voaphylline-vobasinyl type bisindole alkaloids, a structural type previously unknown, while 3-6 exhibited cytotoxicity against three human cancer cell lines HeLa, MCF-7, and SW480 with IC50 values ranging from 1.42 to 11.35 μM.
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Cites background from "Sarpagin, ein neues Alkaloid aus Ra..."
..., 1967a), and the presence of seven methines dC from 60 to 30 also indicated that the other unit was a vobasine (sarpapan)-type (Sroll and Hofmann, 1953)....
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...The only upfield quaternary carbon, at dC 33.2, is a characteristic resonance of C-200 in the voaphylline unit (Kunesch et al., 1967a), and the presence of seven methines dC from 60 to 30 also indicated that the other unit was a vobasine (sarpapan)-type (Sroll and Hofmann, 1953)....
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