Asymmetric synthesis of a tricyclic benzofuran motif : A privileged core structure in biologically active molecules
Sundén, Henrik and Olsson, Roger LU
(2010)
In Organic and Biomolecular Chemistry
8(21).
p.4831-4833
- Abstract
An efficient synthetic strategy for the asymmetric synthesis of a hexahydrodibenzofuran core structure, with a quaternary stereogenic center, emerges by employing a chiral reduction using Corey's (S)-Me-CBS-oxazaborolidine reagent followed by a Mitsunobu reaction to set the stereochemistry. A Pd-mediated intramolecular Heck reaction concludes the tricyclic core structure. Finally, a Pd/C catalyzed reduction yields the target molecule in 21% overall yield over 6 steps.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/a8fb82b5-4482-4317-924c-7e019ec1be6c
- author
- Sundén, Henrik
and Olsson, Roger
LU
- publishing date
- 2010-11-07
- type
- Contribution to journal
- publication status
- published
- in
- Organic and Biomolecular Chemistry
- volume
- 8
- issue
- 21
- pages
- 3 pages
- publisher
- Royal Society of Chemistry
- external identifiers
-
- scopus:77957899918
- pmid:20835457
- ISSN
- 1477-0520
- DOI
- 10.1039/c0ob00331j
- language
- English
- LU publication?
- no
- id
- a8fb82b5-4482-4317-924c-7e019ec1be6c
- date added to LUP
- 2019-10-02 10:10:59
- date last changed
- 2024-04-16 21:18:51
@article{a8fb82b5-4482-4317-924c-7e019ec1be6c,
abstract = {{<p>An efficient synthetic strategy for the asymmetric synthesis of a hexahydrodibenzofuran core structure, with a quaternary stereogenic center, emerges by employing a chiral reduction using Corey's (S)-Me-CBS-oxazaborolidine reagent followed by a Mitsunobu reaction to set the stereochemistry. A Pd-mediated intramolecular Heck reaction concludes the tricyclic core structure. Finally, a Pd/C catalyzed reduction yields the target molecule in 21% overall yield over 6 steps.</p>}},
author = {{Sundén, Henrik and Olsson, Roger}},
issn = {{1477-0520}},
language = {{eng}},
month = {{11}},
number = {{21}},
pages = {{4831--4833}},
publisher = {{Royal Society of Chemistry}},
series = {{Organic and Biomolecular Chemistry}},
title = {{Asymmetric synthesis of a tricyclic benzofuran motif : A privileged core structure in biologically active molecules}},
url = {{http://dx.doi.org/10.1039/c0ob00331j}},
doi = {{10.1039/c0ob00331j}},
volume = {{8}},
year = {{2010}},
}