Assembly of Terpenoid Cores by a Simple, Tunable Strategy

Ouidad Lahtigui; Fabien Emmetiere; Wei Zhang; Liban Jirmo; Samira Toledo-Roy; John C. Hershberger; Jocelyn M. Macho; Alexander J. Grenning

doi:10.1002/anie.201608863

Assembly of Terpenoid Cores by a Simple, Tunable Strategy

Ouidad Lahtigui
, Fabien Emmetiere
, Wei Zhang
, Liban Jirmo
, Samira Toledo-Roy
, John C. Hershberger
, Jocelyn M. Macho
, Alexander J. Grenning

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	15792-15796
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	51
DOIs	https://doi.org/10.1002/anie.201608863
State	Published - Dec 19 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Knoevenagel adducts
[3,3] Cope rearrangement
allylic alkylation
deconjugative alkylation
terpene synthesis

Publisher link

10.1002/anie.201608863

Find It

Find It at U of M Libraries

Cite this

@article{8d4444c3ff4b4547a32714fa17ed199b,

title = "Assembly of Terpenoid Cores by a Simple, Tunable Strategy",

abstract = "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.",

keywords = "Knoevenagel adducts, [3,3] Cope rearrangement, allylic alkylation, deconjugative alkylation, terpene synthesis",

author = "Ouidad Lahtigui and Fabien Emmetiere and Wei Zhang and Liban Jirmo and Samira Toledo-Roy and Hershberger, \{John C.\} and Macho, \{Jocelyn M.\} and Grenning, \{Alexander J.\}",

note = "Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2016",

month = dec,

day = "19",

doi = "10.1002/anie.201608863",

language = "English (US)",

volume = "55",

pages = "15792--15796",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "51",

}

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.

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

UR - https://www.scopus.com/pages/publications/85003646782

UR - https://www.scopus.com/pages/publications/85003646782#tab=citedBy

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 -

Assembly of Terpenoid Cores by a Simple, Tunable Strategy

Abstract

Bibliographical note

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this