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
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.
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.
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.
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.
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
