Publication type: Article in scientific journal
Type of review: Peer review (publication)
Title: Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-ol
Authors: Höck, Stefan
Borschberg, Hans-Jürg
DOI: 10.1002/hlca.200690058
Published in: Helvetica Chimica Acta
Volume(Issue): 89
Issue: 3
Page(s): 542
Pages to: 557
Issue Date: 2006
Publisher / Ed. Institution: Wiley
ISSN: 0018-019X
Language: English
Subjects: Indole alkaloids; Cycloadditions; Bredt's rule; Ireland-Claisen rearrangemenent
Subject (DDC): 572: Biochemistry
Abstract: The first total synthesis of the natural product (−)‐(19R)‐ibogamin‐19‐ol ((−)‐1) is reported (biogenetic atom numbering). Starting with L‐glutamic acid from the chiral pool and (2S)‐but‐3‐en‐2‐ol, the crucial aliphatic isoquinuclidine (= 2‐azabicyclo[2.2.2]octane) core containing the entire configurational information of the final target was prepared in 15 steps (overall yield: 15%). The two key steps involved a highly effective, self‐immolating chirality transfer in an Ireland-Claisen rearrangement and an intramolecular nitrone‐olefin 1,3‐dipolar cycloaddition reaction. Onto this aliphatic core was grafted the aromatic moiety in the form of N(1)‐protected 1H‐indole‐3‐acetic acid by application of the dicyclohexylcarbodiimide (DCC) method. Four additional steps were required to adjust the substitution pattern at C(16) and to deprotect the indole subunit for the closure of the crucial 7‐membered ring present in the targeted alkaloid family. The spectral and chiroptical properties of the final product (−)‐1 matched the ones reported for the naturally occurring alkaloid, which had been isolated from Tabernaemonatana quadrangularis in 1980. The overall yield of the entire synthesis involving a linear string of 20 steps amounted to 1.9% (average yield per step: 82%).
Fulltext version: Published version
License (according to publishing contract): Licence according to publishing contract
Departement: Life Sciences and Facility Management
Organisational Unit: Institute of Chemistry and Biotechnology (ICBT)
Appears in collections:Publikationen Life Sciences und Facility Management

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Höck, S., & Borschberg, H.-J. (2006). Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-ol. Helvetica Chimica Acta, 89(3), 542–557.
Höck, S. and Borschberg, H.-J. (2006) ‘Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-ol’, Helvetica Chimica Acta, 89(3), pp. 542–557. Available at:
S. Höck and H.-J. Borschberg, “Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-ol,” Helvetica Chimica Acta, vol. 89, no. 3, pp. 542–557, 2006, doi: 10.1002/hlca.200690058.
HÖCK, Stefan und Hans-Jürg BORSCHBERG, 2006. Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-ol. Helvetica Chimica Acta. 2006. Bd. 89, Nr. 3, S. 542–557. DOI 10.1002/hlca.200690058
Höck, Stefan, and Hans-Jürg Borschberg. 2006. “Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-Ol.” Helvetica Chimica Acta 89 (3): 542–57.
Höck, Stefan, and Hans-Jürg Borschberg. “Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-Ol.” Helvetica Chimica Acta, vol. 89, no. 3, 2006, pp. 542–57,

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