Leuconolam - CAS 93710-27-1
Catalog number: 93710-27-1
Not Intended for Therapeutic Use. For research use only.
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Leuconolam comes from the herbs of Alstonia scholaris
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1.Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group.
Izgu EC;Hoye TR Chem Sci. 2013 Feb;4(5):2262-2266.
A concise total synthesis of the plant alkaloid (±)-leuconolam (1) has been achieved. A regio- and diastereoselective Lewis-acid mediated allylative cyclization was used to establish, simultaneously, two adjacent tetrasubstituted carbon centers. Furthermore, an essential arene cross-coupling to a hindered haloalkene was enabled by the use of a novel 2-anilinostannane.
2.Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.
Yang Y;Bai Y;Sun S;Dai M Org Lett. 2014 Dec 5;16(23):6216-9. doi: 10.1021/ol503150c. Epub 2014 Nov 20.
Inspired by their potential biosynthesis, we have developed divergent total syntheses of seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam, and one unnatural analogue with an unprecedented structural skeleton. The key steps involve a Witkop-Winterfeldt oxidative indole cleavage followed by transannular cyclization. The transannular cyclization product was then converted to the corresponding structural skeletons by pairing its functional groups into different reaction modes.
3.Transformations of the 2,7-Seco Aspidosperma alkaloid leuconolam, structure revision of epi-leuconolam, and partial syntheses of leuconoxine and leuconodines A and F.
Low YY;Hong FJ;Lim KH;Thomas NF;Kam TS J Nat Prod. 2014 Feb 28;77(2):327-38. doi: 10.1021/np400922x. Epub 2014 Jan 15.
Several transformations of the seco Aspidosperma alkaloid leuconolam were carried out. The based-induced reaction resulted in cyclization to yield two epimers, the major product corresponding to the optical antipode of a (+)-meloscine derivative. The structures and relative configuration of the products were confirmed by X-ray diffraction analysis. Reaction of leuconolam and epi-leuconolam with various acids, molecular bromine, and hydrogen gave results that indicated that the structure of the alkaloid, previously assigned as epi-leuconolam, was incorrect. This was confirmed by an X-ray diffraction analysis, which revealed that epi-leuconolam is in fact 6,7-dehydroleuconoxine. Short partial syntheses of the diazaspiro indole alkaloid leuconoxine and the new leuconoxine-type alkaloids leuconodines A and F were carried out.
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CAS 93710-27-1 Leuconolam

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