Details
| Original language | English |
|---|---|
| Pages (from-to) | 6871-6881 |
| Number of pages | 11 |
| Journal | Journal of the American Chemical Society |
| Volume | 144 |
| Issue number | 15 |
| Early online date | 12 Apr 2022 |
| Publication status | Published - 20 Apr 2022 |
Abstract
Elansolid A is a structurally complex polyketide macrolactone natural product that exhibits promising antibacterial properties. Its challenging asymmetric total synthesis was achieved by a convergent strategy, in which the tetrahydroindane core of the molecule and an eastern vinyl iodide moiety were combined as the main fragments. The central tetrahydroindane motif was constructed with high stereoselectivity by a bioinspired intramolecular Diels-Alder cycloaddition, generating four stereogenic centers in a single step. The stereocontrol of this key step could be achieved by virtue of a 1,3-allylic strain generated by the temporary introduction of a steric-directing iodine substituent on the substrate. The formation of the macrolactone motif that completes the synthesis was achieved via two different retrosynthetic disconnections, namely, a Suzuki-Miyaura cross-coupling or an alternative Mukaiyama esterification reaction.
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- General Chemistry
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemical Engineering(all)
- Colloid and Surface Chemistry
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In: Journal of the American Chemical Society, Vol. 144, No. 15, 20.04.2022, p. 6871-6881.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Asymmetric Total Synthesis of Antibiotic Elansolid A
AU - Wang, Liang Liang
AU - Yu, Qi
AU - Zhang, Wenjing
AU - Yang, Shuai
AU - Peng, Lin
AU - Zhang, Liang
AU - Li, Xiao Nian
AU - Gagosz, Fabien
AU - Kirschning, Andreas
N1 - Funding Information: Financial support for this work was provided by the Youth Innovation Promotion Association CAS and the High-Level Talent Program of Yunnan Province and in part by the Alexander-von-Humboldt foundation for L.L.W.
PY - 2022/4/20
Y1 - 2022/4/20
N2 - Elansolid A is a structurally complex polyketide macrolactone natural product that exhibits promising antibacterial properties. Its challenging asymmetric total synthesis was achieved by a convergent strategy, in which the tetrahydroindane core of the molecule and an eastern vinyl iodide moiety were combined as the main fragments. The central tetrahydroindane motif was constructed with high stereoselectivity by a bioinspired intramolecular Diels-Alder cycloaddition, generating four stereogenic centers in a single step. The stereocontrol of this key step could be achieved by virtue of a 1,3-allylic strain generated by the temporary introduction of a steric-directing iodine substituent on the substrate. The formation of the macrolactone motif that completes the synthesis was achieved via two different retrosynthetic disconnections, namely, a Suzuki-Miyaura cross-coupling or an alternative Mukaiyama esterification reaction.
AB - Elansolid A is a structurally complex polyketide macrolactone natural product that exhibits promising antibacterial properties. Its challenging asymmetric total synthesis was achieved by a convergent strategy, in which the tetrahydroindane core of the molecule and an eastern vinyl iodide moiety were combined as the main fragments. The central tetrahydroindane motif was constructed with high stereoselectivity by a bioinspired intramolecular Diels-Alder cycloaddition, generating four stereogenic centers in a single step. The stereocontrol of this key step could be achieved by virtue of a 1,3-allylic strain generated by the temporary introduction of a steric-directing iodine substituent on the substrate. The formation of the macrolactone motif that completes the synthesis was achieved via two different retrosynthetic disconnections, namely, a Suzuki-Miyaura cross-coupling or an alternative Mukaiyama esterification reaction.
UR - http://www.scopus.com/inward/record.url?scp=85128696051&partnerID=8YFLogxK
U2 - 10.1021/jacs.2c01133
DO - 10.1021/jacs.2c01133
M3 - Article
C2 - 35410472
AN - SCOPUS:85128696051
VL - 144
SP - 6871
EP - 6881
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 15
ER -