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.
Convenient One-Pot Conversion of Alcohols into Esters via Hemiacetal Intermediates
Lichtenthaler, Frieder W.,Jarglis, Pan,Lorenz, Klaus
, p. 790 - 792 (1988)
A simple and efficient one-pot oxidative procedure, adaptable to a large scale, is described for the preparation of methyl esters from either primary alcohols or vic-diols.The aldehyde is generated by Swern or periodate oxidation, followed by bromine oxidation of the methyl hemiacetal formed in aqueous methanolic solution.
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.
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.
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
SUBSTITUTED BIARYL ALKYL AMIDES
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Paragraph 0251, (2013/05/08)
Disclosed herein are substituted biaryl alkyl amide compounds, methods of synthesizing substituted biaryl alkyl amide compounds and methods of treating diseases and/or conditions with substituted biaryl alkyl amide compounds.
Stereoselective total synthesis of both (6R,9R,10S,7E)- and (6S,9R,10S,7E)-epimers of oxylipin (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid
Saikia, Bishwajit,Devi, Thongam Joymati,Barua, Nabin C.
, p. 2157 - 2166 (2013/03/14)
An asymmetric synthesis of both the stereoisomers (2a & 2b) of the structure 2 proposed for (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid, an immunostimulant oxylipin from the n-butanol extract of the corms of Dracontium loretense, has been accomplished. The key steps involved are using Jacobsen's hydrolytic kinetic resolution (HKR), Julia-Kocienski olefination, regioselective epoxide ring opening and Wittig olefination. The configuration (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid was established as 2a from comparison of NMR data, HPLC analysis and [α]D values of naturally derived (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid, and comparison with the synthetic diastereomers 2a and 2b.
Stereoselective total synthesis of (+)-synargentolide A
Prasad, Kavirayani R.,Penchalaiah, Kamala
experimental part, p. 2853 - 2858 (2011/03/18)
The stereoselective synthesis of synargentolide A, a polyhydroxy δ-lactone, has been accomplished from tartaric acid. The key steps in the synthesis involve Keck and Brown allylations and ring closing metathesis.
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
