874896-58-9Relevant academic research and scientific papers
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
, (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.
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 (2015/02/19)
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.
Palladium-catalysed cyclisation of alkenols: Synthesis of oxaheterocycles as core intermediates of natural compounds
Palk, Miroslav,Koek, Jozef,Ko, Peter,Gracza, Tibor
supporting information, p. 2077 - 2086 (2014/12/11)
The study of Pd-catalysed cyclisation reactions of alkenols using different catalytic systems is reported. These transformations affect the stereoselective construction of mono- and/or bicyclic oxaheterocyclic derivatives depending on a starting alkenol. The substrate scope and proposed mechanism of Pd-catalysed cyclisation reactions are also discussed. Moreover, the diastereoselectivePd-catalysed cyclisation of appropriate alkenols to tetrahydrofurans and subsequent cyclisation provided properly substituted 2,5-dioxabicyclo[2.2.1]heptane and 2,6-dioxabicyclo[3.2.1]octane, respectively. Such bicyclic ring subunits are found in many natural products including ocellenynes and aurovertines.
Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to α-chiral aldehydes: Formal synthesis of all eight L-hexoses
Man, Soo Bong,Kong, Jong Rock,Krische, Michael J.
supporting information; experimental part, p. 4133 - 4135 (2009/05/27)
(Chemical Equation Presented) Hydrogenative coupling of acetylene to α-chiral aldehydes 1a-4a using enantiomeric rhodium catalysts ligated by (S)-MeO-BIPHEP and (R)-MeO-BIPHEP delivers the diastereomeric products of carbonyl-(Z)-buladienylation 1b-4b and 1c-4c, respectively, with good to excellent levels of catalyst directed diastereofacial selectivity. Diastereomeric L-glyceraldehyde acetonide adducts 1b and 1c were converted to the four isomeric enoates 6b, 8b, 6c, and 8c, representing a formal synthesis of all eight L-hexoses.
Total synthesis of hyacinthacine A1, a glycosidase inhibitor
Chandrasekhar, Srivari,Parida, Bibhuti Bhusan,Rambabu, Chegondi
, p. 7826 - 7828 (2008/12/22)
(Chemical Equation Presented) A practical and enantioselective total synthesis of hyacinthacine A1 is achieved involving syn allylic epoxide opening with retention using Pd catalysis and "domino" hydrogenation (five steps in one pot) sequences.
Diastereoselective synthesis of all eight L-hexoses from L-ascorbic acid
Ermolenko, Ludmila,Sasaki, N. Andre
, p. 693 - 703 (2007/10/03)
A novel versatile method for the synthesis of all eight diastereomerically pure L-hexoses was developed. L-Ascorbic acid was converted to two diastereomers A. These α-hydroxy esters were transformed into four γ-alkoxy- α,β-unsaturated esters C via the int
