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 -