Stereocontrolled synthesis of lepadiformine A
Publication type: Journal Article
Publication date: 2008-07-02
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
DOI:
10.1039/b805951a
PubMed ID:
18698466
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
In this paper we present results of a study into whether the tricyclic core of the lepadiformines A-C can be accessed via intramolecular hetero-Diels-Alder cycloaddition. We are able to demonstrate that such a process is possible and that the reaction proceeds in an endo-selective fashion, providing the correct relative stereochemistry for this family of natural products. By employing this approach we have been able to develop a short (7 step) synthesis of (+/-)-lepadiformine A, starting from commercially-available trans-2-nonenal.
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Metrics
29
Total citations:
29
Citations from 2024:
4
(13.79%)
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MLA
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GOST
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Lygo B., Kirton E. H., Lumley C. Stereocontrolled synthesis of lepadiformine A // Organic and Biomolecular Chemistry. 2008. Vol. 6. No. 17. p. 3085.
GOST all authors (up to 50)
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Lygo B., Kirton E. H., Lumley C. Stereocontrolled synthesis of lepadiformine A // Organic and Biomolecular Chemistry. 2008. Vol. 6. No. 17. p. 3085.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/b805951a
UR - https://doi.org/10.1039/b805951a
TI - Stereocontrolled synthesis of lepadiformine A
T2 - Organic and Biomolecular Chemistry
AU - Lygo, Barry
AU - Kirton, Eirene H.M.
AU - Lumley, Christopher
PY - 2008
DA - 2008/07/02
PB - Royal Society of Chemistry (RSC)
SP - 3085
IS - 17
VL - 6
PMID - 18698466
SN - 1477-0520
SN - 1477-0539
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2008_Lygo,
author = {Barry Lygo and Eirene H.M. Kirton and Christopher Lumley},
title = {Stereocontrolled synthesis of lepadiformine A},
journal = {Organic and Biomolecular Chemistry},
year = {2008},
volume = {6},
publisher = {Royal Society of Chemistry (RSC)},
month = {jul},
url = {https://doi.org/10.1039/b805951a},
number = {17},
pages = {3085},
doi = {10.1039/b805951a}
}
Cite this
MLA
Copy
Lygo, Barry, et al. “Stereocontrolled synthesis of lepadiformine A.” Organic and Biomolecular Chemistry, vol. 6, no. 17, Jul. 2008, p. 3085. https://doi.org/10.1039/b805951a.