TY - JOUR
T1 - Enantiospecific Entry to a Common Decalin Intermediate for the Syntheses of Highly Oxygenated Terpenoids
AU - Nagasawa, Shota
AU - Jones, Kerry E.
AU - Sarpong, Richmond
N1 - Funding Information:
We thank College of Chemistry’s NMR facility for resources provided and the staff for their assistance. Instruments in CoC-NMR are supported in part by NIH S10OD024998 and the Catalysis Facility of Lawrence Berkeley National Laboratory, which is supported by the Director, Office of Science, of the U.S. Department of Energy under Contract No. DE-AC02-05CH11231.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/9/20
Y1 - 2019/9/20
N2 - Herein, we describe an enantiospecific route to one enantiomer of a common decalin core that is present in numerous highly oxygenated terpenoids. This intermediate is accessed in eight steps from (R)-carvone, an inexpensive, enantioenriched building block, which can be elaborated to the desired bicycle through sequential Fe(III)-catalyzed reductive olefin coupling and Dieckmann condensation. The same synthetic route may be applied to (S)-carvone to afford the enantiomer of this common intermediate for other applications.
AB - Herein, we describe an enantiospecific route to one enantiomer of a common decalin core that is present in numerous highly oxygenated terpenoids. This intermediate is accessed in eight steps from (R)-carvone, an inexpensive, enantioenriched building block, which can be elaborated to the desired bicycle through sequential Fe(III)-catalyzed reductive olefin coupling and Dieckmann condensation. The same synthetic route may be applied to (S)-carvone to afford the enantiomer of this common intermediate for other applications.
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U2 - 10.1021/acs.joc.9b01937
DO - 10.1021/acs.joc.9b01937
M3 - Article
C2 - 31454485
AN - SCOPUS:85072508599
SN - 0022-3263
VL - 84
SP - 12209
EP - 12215
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 18
ER -