| 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 1522-2675 |
| 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%). |
| URI: | https://digitalcollection.zhaw.ch/handle/11475/11999 |
| 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 |
Files in This Item:
There are no files associated with this item.
Show full item record
Höck, S., & Borschberg, H.-J. (2006). Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-ol. Helvetica Chimica Acta, 89(3), 542–557. https://doi.org/10.1002/hlca.200690058
Höck, S. and Borschberg, H.-J. (2006) ‘Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-ol’, Helvetica Chimica Acta, 89(3), pp. 542–557. Available at: https://doi.org/10.1002/hlca.200690058.
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. https://doi.org/10.1002/hlca.200690058.
Höck, Stefan, and Hans-Jürg Borschberg. “Enantioselective Synthesis of (−)-(19R)-Ibogamin-19-Ol.” Helvetica Chimica Acta, vol. 89, no. 3, 2006, pp. 542–57, https://doi.org/10.1002/hlca.200690058.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.