100906-42-1Relevant articles and documents
Formal syntheses of (2R,3R)-3-hydroxy pipecolic acid and (2R,3S)-3-hydroxy pipecolic acid from l-ascorbic acid
Chavan, Subhash P.,Dumare, Nilesh B.,Pawar, Kailash P.
, p. 805 - 807 (2015)
Formal syntheses of both cis and trans 3-hydroxy pipecolic acids is achieved from l-ascorbic acid. Present synthesis describes use of chiral pool approach in which epimerization, Staudinger reaction and Cyclization reactions were employed as key steps.
Synthesis of C1–C11 eribulin fragment and its diastereomeric analogues
Khatravath, Mahender,Mallurwar, Naveen Kumar,Konda, Saidulu,Gaddam, Jagan,Rao, Pallavi,Iqbal, Javed,Arya, Prabhat
supporting information, (2019/07/17)
A practical stereoselective synthesis of the central C1–C10 fragment of eribulin and its two diastereomeric analogues is developed. Our approach relied on the use of L-ascorbic acid as the starting material which allowed accessing a key intermediate with a syn diol moiety (C9 and C10 of eribulin) and a carboxylic ester group. A functionalized six membered lactone having several required hydroxyl groups was then obtained. In a number of steps, the lactone was converted to an intermediate for our key oxa-Michael reaction. A regio- and stereocontrolled intramolecular oxa-Michael reaction completed the synthesis of the C1–11 fragment having a trans-fused tetrahydropyrans with the exact stereochemistry of various hydroxyl groups, as in eribulin.
Facile synthesis of (2R,3S)-2-benzyloxy-3-hydroxybutyrolactone
El-Batta, Amer
, p. 2457 - 2463 (2013/07/25)
The heterocyclic diols derived from L-dimethyl tartrate are important chiral synthons in organic synthesis. In particular, L-threosolactone and L-threosolactam structures are versatile precursors for the synthesis of biologically active molecules. Structu
