TY - JOUR
T1 - Assembly of Terpenoid Cores by a Simple, Tunable Strategy
AU - Lahtigui, Ouidad
AU - Emmetiere, Fabien
AU - Zhang, Wei
AU - Jirmo, Liban
AU - Toledo-Roy, Samira
AU - Hershberger, John C.
AU - Macho, Jocelyn M.
AU - Grenning, Alexander J.
N1 - Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2016/12/19
Y1 - 2016/12/19
N2 - Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid-like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.
AB - Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid-like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.
KW - Knoevenagel adducts
KW - [3,3] Cope rearrangement
KW - allylic alkylation
KW - deconjugative alkylation
KW - terpene synthesis
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U2 - 10.1002/anie.201608863
DO - 10.1002/anie.201608863
M3 - Article
AN - SCOPUS:85003646782
SN - 1433-7851
VL - 55
SP - 15792
EP - 15796
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 51
ER -