Synthesis of vinca alkaloids and related compounds. 63. A new synthetic pathway for preparing alkaloids and related compounds with the aspidosperma skeleton. Total syntheses of (±)-vincadifformine, (±)-tabersonine, and (±)-3-oxotabersonine

György Kalaus, István Greiner, M. Kajtár-Peredy, János Brlik, Lajos Szabó, Csaba Szántay

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51 Citations (Scopus)

Abstract

Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (±)-vincadifformine (4), (±)-3-oxotabersonine (42), and (±)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.

Original languageEnglish
Pages (from-to)1434-1442
Number of pages9
JournalJournal of Organic Chemistry
Volume58
Issue number6
Publication statusPublished - 1993

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Vinca Alkaloids
Alkaloids
Esters
Cycloaddition
Benzoates
Chlorides
tabersonine
vincadifformine
indole
tryptamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis of vinca alkaloids and related compounds. 63. A new synthetic pathway for preparing alkaloids and related compounds with the aspidosperma skeleton. Total syntheses of (±)-vincadifformine, (±)-tabersonine, and (±)-3-oxotabersonine",
abstract = "Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (±)-vincadifformine (4), (±)-3-oxotabersonine (42), and (±)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.",
author = "Gy{\"o}rgy Kalaus and Istv{\'a}n Greiner and M. Kajt{\'a}r-Peredy and J{\'a}nos Brlik and Lajos Szab{\'o} and Csaba Sz{\'a}ntay",
year = "1993",
language = "English",
volume = "58",
pages = "1434--1442",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
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TY - JOUR

T1 - Synthesis of vinca alkaloids and related compounds. 63. A new synthetic pathway for preparing alkaloids and related compounds with the aspidosperma skeleton. Total syntheses of (±)-vincadifformine, (±)-tabersonine, and (±)-3-oxotabersonine

AU - Kalaus, György

AU - Greiner, István

AU - Kajtár-Peredy, M.

AU - Brlik, János

AU - Szabó, Lajos

AU - Szántay, Csaba

PY - 1993

Y1 - 1993

N2 - Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (±)-vincadifformine (4), (±)-3-oxotabersonine (42), and (±)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.

AB - Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (±)-vincadifformine (4), (±)-3-oxotabersonine (42), and (±)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.

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