Aza-Diels-Alder/intramolecular Heck cyclization approach to the tetrahydro-β-carboline skeleton of the ajmaline/sarpagine alkaloids

Jeffrey T. Kuethe; Audrey Wong; Ian W. Davies; Paul J. Reider

doi:10.1016/S0040-4039(02)00668-8

Aza-Diels-Alder/intramolecular Heck cyclization approach to the tetrahydro-β-carboline skeleton of the ajmaline/sarpagine alkaloids

Jeffrey T. Kuethe
, Audrey Wong
, Ian W. Davies
, Paul J. Reider

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

The aza-Diels-Alder reactions of 2-iodo-3-indoleacetaldehydes in the presence of zinc triflate provides 2-(2-iodoindolylmethyl)-4-pyridones in high yield. Palladium-mediated intramolecular Heck cyclization gives access to the tetracyclic tetrahydro-β-carboline framework of the ajmaline/sarpagine alkaloids.

Original language	English (US)
Pages (from-to)	3871-3874
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(02)00668-8
State	Published - May 20 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)00668-8

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title = "Aza-Diels-Alder/intramolecular Heck cyclization approach to the tetrahydro-β-carboline skeleton of the ajmaline/sarpagine alkaloids",

abstract = "The aza-Diels-Alder reactions of 2-iodo-3-indoleacetaldehydes in the presence of zinc triflate provides 2-(2-iodoindolylmethyl)-4-pyridones in high yield. Palladium-mediated intramolecular Heck cyclization gives access to the tetracyclic tetrahydro-β-carboline framework of the ajmaline/sarpagine alkaloids.",

author = "Kuethe, \{Jeffrey T.\} and Audrey Wong and Davies, \{Ian W.\} and Reider, \{Paul J.\}",

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doi = "10.1016/S0040-4039(02)00668-8",

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AU - Kuethe, Jeffrey T.

AU - Wong, Audrey

AU - Davies, Ian W.

AU - Reider, Paul J.

PY - 2002/5/20

Y1 - 2002/5/20

N2 - The aza-Diels-Alder reactions of 2-iodo-3-indoleacetaldehydes in the presence of zinc triflate provides 2-(2-iodoindolylmethyl)-4-pyridones in high yield. Palladium-mediated intramolecular Heck cyclization gives access to the tetracyclic tetrahydro-β-carboline framework of the ajmaline/sarpagine alkaloids.

AB - The aza-Diels-Alder reactions of 2-iodo-3-indoleacetaldehydes in the presence of zinc triflate provides 2-(2-iodoindolylmethyl)-4-pyridones in high yield. Palladium-mediated intramolecular Heck cyclization gives access to the tetracyclic tetrahydro-β-carboline framework of the ajmaline/sarpagine alkaloids.

UR - https://www.scopus.com/pages/publications/0037140864

UR - https://www.scopus.com/pages/publications/0037140864#tab=citedBy

U2 - 10.1016/S0040-4039(02)00668-8

DO - 10.1016/S0040-4039(02)00668-8

M3 - Article

AN - SCOPUS:0037140864

SN - 0040-4039

VL - 43

SP - 3871

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Aza-Diels-Alder/intramolecular Heck cyclization approach to the tetrahydro-β-carboline skeleton of the ajmaline/sarpagine alkaloids

Abstract

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