123164-32-9Relevant academic research and scientific papers
An oxidative dearomatization-induced [5 + 2] cascade enabling the syntheses of α-cedrene, α-pipitzol, and sec -cedrenol
Green, Jason C.,Pettus, Thomas R. R.
supporting information; experimental part, p. 1603 - 1608 (2011/04/16)
Efficient syntheses of α-cedrene (1), α-pipitzol (2), and sec-cedrenol (3) were carried out using a new method, which was inspired by the proposed biosynthesis of the tricyclic skeleton of cedrol (12). The key transformation begins with the oxidative dearomatization of curcuphenol (5a) followed by an intramolecular [5 + 2] cycloaddition of the respective phenoxonium intermediate across the tethered olefin. The benzylic stereocenter effectively guides the formation of the first two stereocenters during the [5 + 2] reaction. The cascade then terminates with the selective incorporation of acetic acid to generate a third stereocenter, setting it apart from other previous cationic [5 + 2] reactions. The phenolic precursors (5a-h) are constructed from readily available salicylaldehydes, either as the racemate (one pot) or as a specific enantiomer (four pots) by a modification to our method for the generation of ortho-quinone methides (o-QMs).
Enantioselective total synthesis of (-)-curcuquinone via regioselective chromium-mediated benzannulation
Minatti, Ana,Doetz, Karl Heinz
, p. 3745 - 3748 (2007/10/03)
(Chemical Equation Presented) A short and efficient, high-yielding enantioselective total synthesis of the marine natural product (-)-curcuquinone 1 is reported involving a regioselective [3 + 2 + 1]-benzannulation reaction as the key step. Additionally, this strategy allows the isolation of curcuhydroquinone monomethyl ether 9 as an intermediate of the benzannulation reaction and its subsequent further protection toward diversified hydroquinones.
Formal syntheses of heliannuols A and D, allelochemicals from Helianthus annus
Tuhina, Kazi,Bhowmik, Dipal R.,Venkateswaran, Ramanathapuram V.
, p. 634 - 635 (2007/10/03)
A synthesis of heliannuol A 1 is described involving hydrogenolysis of the cyclopropane fused benzoxepane compound 23 to generate the benzoxocane ring system of 1 and a fragmentation of methyl ether 25 furnished 4-methoxycurcuphenol 29, an advanced interm
Total synthesis of (±)-heliannuol D, an allelochemical from Helianthus annuus
Vyvyan, James R.,Looper, Ryan E.
, p. 1151 - 1154 (2007/10/03)
The total synthesis of (±)-heliannuol D and its epimer has been completed in 9 steps and 12% overall yield from 2-methylanisole. The benzoxepane moiety of the title compound, a common structural feature in the heliannuol family of natural products, is pre
