TY - JOUR
T1 - Pd(II)-Catalyzed Synthesis of Bicyclo[3.2.1] Lactones via Tandem Intramolecular β-C(sp3)-H Olefination and Lactonization of Free Carboxylic Acids
AU - Tomanik, Martin
AU - Qian, Shaoqun
AU - Yu, Jin Quan
N1 - Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/7/13
Y1 - 2022/7/13
N2 - Bicyclo[3.2.1] lactones are chemical scaffolds found in numerous bioactive natural products. Herein, we detail the development of a novel palladium(II)-catalyzed tandem intramolecular β-C(sp3)-H olefination and lactonization reaction that rapidly transforms linear carboxylic acid possessing a tethered olefin into the bicyclo[3.2.1] lactone motif. This transformation features a broad substrate scope, shows excellent functional group compatibility, and can be extended to the preparation of the related seven-membered bicyclo[4.2.1] lactones. Additionally, we demonstrate the synthetic potential of this annulation by constructing the 6,6,5-tricyclic lactone core structure of the meroterpenoid cochlactone A. We anticipate that this compelling reaction may provide a novel synthetic disconnection that can be broadly applied toward the preparation of a variety of bioactive natural products.
AB - Bicyclo[3.2.1] lactones are chemical scaffolds found in numerous bioactive natural products. Herein, we detail the development of a novel palladium(II)-catalyzed tandem intramolecular β-C(sp3)-H olefination and lactonization reaction that rapidly transforms linear carboxylic acid possessing a tethered olefin into the bicyclo[3.2.1] lactone motif. This transformation features a broad substrate scope, shows excellent functional group compatibility, and can be extended to the preparation of the related seven-membered bicyclo[4.2.1] lactones. Additionally, we demonstrate the synthetic potential of this annulation by constructing the 6,6,5-tricyclic lactone core structure of the meroterpenoid cochlactone A. We anticipate that this compelling reaction may provide a novel synthetic disconnection that can be broadly applied toward the preparation of a variety of bioactive natural products.
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U2 - 10.1021/jacs.2c04195
DO - 10.1021/jacs.2c04195
M3 - Article
C2 - 35763801
AN - SCOPUS:85134426894
SN - 0002-7863
VL - 144
SP - 11955
EP - 11960
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 27
ER -