160699-77-4Relevant academic research and scientific papers
Total Synthesis of 5-Hydroxygoniothalamin
Patpi, Santhosh Reddy,Jin, Guangyi,Kantevari, Srinivas
, p. 780 - 786 (2019/01/23)
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.
Stereoselective Synthesis of C1–C7 and C6–C22 Fragments of Phostriecin, Goniothalamines, and Their Analogues
Purushotham Reddy,Vasudeva Reddy,Sabitha, Gowravaram
, p. 4389 - 4399 (2018/09/11)
The stereoselective synthesis of two fragments (C1–C7 and C6–C22) of the anti-tumor agent phostriecin has been achieved. The chiral hydroxy-vinyl-δ-lactone building block (fragment C1–C7) was subsequently utilized for the synthesis of 5-hydroxygoniothalamin, 5-acetoxygoniothalamin, and their derivatives.
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
