131581-04-9Relevant articles and documents
Assembly of Terpenoid Cores by a Simple, Tunable Strategy
Lahtigui, Ouidad,Emmetiere, Fabien,Zhang, Wei,Jirmo, Liban,Toledo-Roy, Samira,Hershberger, John C.,Macho, Jocelyn M.,Grenning, Alexander J.
, p. 15792 - 15796 (2016)
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.
METHODS AND COMPOSITIONS FOR TERPENOID SYNTHESIS
-
, (2018/04/13)
In one aspect, the disclosure relates to methods for preparation of terpene and terpene-like molecules. In a further aspect, the disclosure relates to the products of the disclosed methods, i.e., terpene and terpene-like molecules prepared using the disclosed methods. Intermediates for the synthesis of a wide variety of terpenoids are γ-allyl Knoevenagel adducts or quasi γ-allyl Knoevenagel adducts are disclosed. In various aspects, methods of preparing terpenoids through these intermediates are disclosed. The methods can comprise α-alkylation of an allylic electrophile followed by ring-closure metathesis to a polycyclic terpenoid structure. In a further aspect, the disclosure pertains to terpenoid frameworks, and compounds prepared via disclosed oxidation and substitution reactions on the disclosed terpenoid frameworks. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
Synthetic Studies on Wedeligenin: Preparation of 3-Hydroxy-Substituted Decalincarbonitriles as a Model for 'A Ring' Annulation
MacLeod, John K.,Molinski, Tadeusz F.
, p. 1309 - 1326 (2007/10/02)
Six new 3-hydroxydecalincarbonitriles were synthesized by employing an annulation strategy involving intramolecular alkylation of 5-bromoalkyl substituted malononitriles or acetonitriles. 2-Allyl-2-methylcyclohexanone was condensed with malononitrile to g
