302348-89-6Relevant academic research and scientific papers
Total Synthesis of 5-Hydroxygoniothalamin
Patpi, Santhosh Reddy,Jin, Guangyi,Kantevari, Srinivas
, p. 780 - 786 (2019)
The total synthesis of 5-hydroxygoniothalamin is achieved from commercially available l -xylose. The α,β-unsaturated-δ-lactone core is constructed in very good yield by utilizing one-carbon and two-carbon cis -Wittig olefinations and δ-lactonization using Yamaguchi conditions. Subsequent Grubbs cross-metathesis followed by desilylation results in 5-hydroxygoniothalamin.
A convergent Pd-catalyzed asymmetric allylic alkylation of dl- And meso-divinylethylene carbonate: Enantioselective synthesis of (+)-australine hydrochloride and formal synthesis of isoaltholactone
Trost, Barry M.,Aponick, Aaron,Stanzl, Benjamin N.
, p. 9547 - 9560 (2008/12/20)
The use of a mixture of dl-and meso-divinylethylene carbonate as an electrophile in palladium-catalyzed asymmetric allylic alkylation reactions is reported. From the diastereomeric mixture of meso and chiral racemic starting materials, a single product is obtained in high optical purity employing either oxygen or nitrogen nucleophiles. The resulting dienes have proven to be versatile synthetic intermediates as each carbon is functionalized for further transformation and differentiated by virtue of the reaction. A mechanism for this intriguing transformation is proposed and a concise enantioselective total synthesis of (+)-australine hydrochloride is reported as well as a formal synthesis of isoaltholactone.
An olefination approach to the enantioselective syntheses of several styryllactones
Harris, Joel M,O'Doherty, George A
, p. 5161 - 5171 (2007/10/03)
A flexible enantioselective route to highly functionalized α,β-unsaturated δ-lactones, has allowed for the syntheses of the styryllactones: altholactone, isoaltholactone, 3-epi-altholactone, 2-epi-altholactone and 5-hydroxy goniothalamin in 2.5, 10, 5, 1 and 13% overall yields from furfural, respectively. This approach derives its asymmetry by applying the Sharpless catalytic asymmetric dihydroxylation to vinylfuran. The resulting diols are produced in high enantioexcess and can be stereoselectively transformed into α,β-unsaturated-δ-lactones via a short highly diastereoselective oxidation and reduction sequence. Wittig olefination or Julia olefination reactions were used to introduce the phenyl group side chain either cis or trans selectively and these intermediates were further elaborated into the altholactone isomers via selective epoxidation reactions.
Enantioselective syntheses of isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin
Harris, Joel M.,O'Doherty, George A.
, p. 2983 - 2986 (2007/10/03)
A flexible enantioselective route to highly functionalized γ,β-unsaturated δ-lactones has allowed for the syntheses of the styryllactones: isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin in 10%, 5%, and 13% overall yields from furfural, re
