75283-35-1Relevant articles and documents
Investigations into nicotinic acetylcholine receptor (nAChR) antagonists: Synthesis of a sub-unit of methyllycaconitine
Baillie, Lynn C.,Bearder, John R.,Sherringham, John A.,Whiting, Donald A.
, p. 2687 - 2688 (1997)
A potentially toxophoric subunit of methyllycaconitine has been synthesised from penta-1,4-dien-3-ol in 14 steps and 5% overall yield.
Two-step labeling of endogenous enzymatic activities by Diels-Alder ligation
Willems, Lianne I.,Verdoes, Martijn,Florea, Bogdan I.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.
experimental part, p. 1769 - 1781 (2011/04/18)
A ligation strategy based on the Diels-Alder [4+2] cycloaddition for the two-step activity-based labeling of endogenously expressed enzymes in complex biological samples has been developed. A panel of four diene-derivatized proteasome probes was synthesized, along with a dienophile-functionalized BODIPY(TMR) tag. These probes were applied in a Diels-Alder labeling procedure that enabled us to label active proteasome β-subunits selectively in cellular extracts and in living cells. We were also able to label the activity of cysteine proteases in cell extracts by utilizing a diene-derivatized cathepsin probe. Importantly, the Diels-Alder strategy described here is fully orthogonal with respect to the Staudinger-Bertozzi ligation, as demonstrated by the independent labeling of different proteolytic activities by the two methods in a single experiment.
Synthesis of the A/E/F sections of conaconitine, napelline and related diterpenoid alkaloids of the aconitine group
Baillie, Lynn C.,Batsanov, Andrei,Bearder, John R.,Whiting, Donald A.
, p. 3471 - 3478 (2007/10/03)
The tricyclic amines (±)-2; R = H and R = Me with five stereogenic centres, representing the A/E/F ring system of the title alkaloids, have been synthesised from penta-1,4-dien-3-ol in eight (overall yield 20%) and nine steps (overall yield 16%) respectively.
Studies into the synthesis of a sub-unit of the neurotoxic alkaloid methyllycaconitine
Baillie, Lynn C.,Bearder, John R.,Li, Wang-Shi,Sherringham, John A.,Whiting, Donald A.
, p. 4047 - 4055 (2007/10/03)
A potentially toxophoric subunit of methyllycaconitine has been synthesised from penta-1,4-dien-3-ol as the mixture of diastereomers 2a and 2b, in 14 steps and 5% overall yield.
Cyclopentene Annulation via Intramolecular Addition of Diazo Ketones to 1,3-Dienes. Applications to the Synthesis of Cyclopentanoid Terpenes
Hudlicky, Tomas,Koszyk, Francis J.,Kutchan, Toni M.,Sheth, Jagdish P.
, p. 5020 - 5027 (2007/10/02)
Initial model studies investigating the utility of a new intramolecular cyclopentene annulation procedure are described as pertaining to the preparation of bicyclooctenones.Several 1-diazo-5,7-octadien-2-ones substituted at the 1-, 7-, or 8-position were decomposed in the presence of Cu(acac)2 to yield stereospecifically the corresponding vinylcyclopropanes 13, 16, 21, 24, and 27.The thermal as well as the rhodium-promoted modes of rearrangement to the appropriate cyclopentenes 14, 17, 22a,b, and 28a,b were studied.Where necessary, diastereomers were separatedand structurally assigned by relying on 13C NMR spectroscopy. 13C NMR data are provided for all new compounds in the bicyclooctane series to serve as an aid in assignments of cyclopentanoid terpenes synthesized by this methodology.The intramolecular cylopropanation-rearrangement sequence of dienic diazo ketones has been shown to provide facile access to bicyclooctanes of the type 14, 17, 22a,b, and 25a,b which are of value as terpene synthons.Enhanced stereoselectivity was observed in the rhodium-promoted cyclopentene rearrangements in favor of the less concave diastereomers (22a, 25a, and 28a).Finally, the sesquiterpene hirsutene (31) was synthesized in 37percent overall yield by this methodology. 13C NMR data for several tricyclo2,6>undecane compounds are also provided.
