14225-07-1Relevant articles and documents
Organocatalytic 1,4-conjugate addition of ascorbic acid to α,β-unsaturated aldehydes: Bio-inspired total syntheses of leucodrin, leudrin and proposed structure of dilaspirolactone
Wang, Zhaofeng,Zhao, Kun,Fu, Junkai,Zhang, Junlin,Yin, Weiyu,Tang, Yefeng
supporting information, p. 2093 - 2097 (2013/04/23)
The organocatalytic additions of ascorbic acid to various α,β-unsaturated aldehydes via tandem 1,4-conjugate addition/hemiacetalization/hemiketalization were developed, which provided a rapid entry into the 5-5-5 spirodilactone cores of a family of ascorbylated natural products. Based on the described chemistry, total syntheses of leucodrin, leudrin and the proposed structure of dilaspirolactone were achieved. The Royal Society of Chemistry 2013.
Vitamin C in Organic Synthesis: Reaction with p-Hydroxybenzyl Alcohol Derivatives
Poss, Andrew J.,Belter, Randolph K.
, p. 1535 - 1540 (2007/10/02)
The reaction of L-ascorbic acid (1) with p-hydroxybenzyl alcohol (9) yields 2-(p-hydroxybenzyl)-3-ketohexulosonic acid lactone (10).This reaction proceeds by the addition of the conjugate base of ascorbic acid to the protonated quinone methide derived fro
THE TOTAL SYNTHESIS OF DELESSERINE, LEUCODRIN, AND DILASPIROLACTONE AGLYCONE
Poss, A. J.,Belter, R. K.
, p. 2555 - 2558 (2007/10/02)
The synthesis of delesserine, 1, leucodrin, 2, and dilaspirolactone aglycone, 3, are reported.The preparation of these ascorbigens was implemented by the addition of ascorbic acid to a p-hydroxy benzyl alcohol derived quinone methide.
