99902-66-6Relevant academic research and scientific papers
First asymmetric total synthesis of aspergillide D
Jena, Bighnanshu K.,Reddy, G. Sudhakar,Mohapatra, Debendra K.
supporting information, p. 1863 - 1871 (2017/03/09)
The first asymmetric total synthesis of a 16-membered macrolide, aspergillide D, is described. The chiral centers of the acid are derived from d-ribose and the alcohol subunit from 1,8-octane diol through Sharpless kinetic resolution, respectively. The other key reactions include Yamaguchi esterification, ring-closing metathesis reaction, and Shiina macrolactonization to construct the fully functionalized macrocycle.
Stereoselective Total Synthesis of Carolacton
Kuilya, Tapan Kumar,Goswami, Rajib Kumar
supporting information, p. 2366 - 2369 (2017/05/12)
A short and convergent strategy for the stereoselective total synthesis of biologically active natural product carolacton has been accomplished. Our synthesis highlights the Urpi acetal aldol, Crimmins aldol, Ireland-Claisen rearrangement, TiCl4/sub
Studies toward the total synthesis of carolacton
Sabitha, Gowravaram,Shankaraiah,Prasad, M.Nagendra,S. Yadav, Jhillu
, p. 251 - 259 (2013/02/23)
An efficient synthesis of the C1-C19 segment of carolacton is described, starting from d-ribose, (-)-β-citronellene and a homopropargylic alcohol, and which employs a Nozaki-Hiyama-Kishi (NHK) coupling as the key step. Other important steps are cross-metathesis and Evans aldol reactions. Georg Thieme Verlag Stuttgart New York.
Nitroxyl radical/PhI(OAc)2: One-pot oxidative cleavage of vicinal diols to (di)carboxylic acids
Shibuya, Masatoshi,Shibuta, Takuro,Fukuda, Hayato,Iwabuchi, Yoshiharu
supporting information, p. 5010 - 5013 (2013/01/15)
A mild and user-friendly one-pot oxidative cleavage of vicinal diols to their corresponding (di)carboxylic acids using AZADOs and PhI(OAc)2 is described. 1,2-Diols and 2,3-diols as well as 1,2,3-triol gave one- or two-carbon-unit-shorter carboxylic acids. Internal vicinal diols also smoothly underwent one-pot oxidative cleavage to afford the corresponding dicarboxylic acids. Cyclic vicinal diols are converted to their corresponding open-form dicarboxylic acids.
Synthesis of screening substrates for the directed evolution of sialic acid aldolase: Towards tailored enzymes for the preparation of influenza a sialidase inhibitor analogues
Woodhall, Thomas,Williams, Gavin,Berry, Alan,Nelson, Adam
, p. 1795 - 1800 (2007/10/03)
The stereoselective synthesis of two epimeric screening substrates, (4R, 5R, 6R)- and (4S, 5R, 6R)-6-dipropylcarbamoyl-2-oxo-4,5,6-trihydroxy-hexanoic acid, for the directed evolution of sialic acid aldolase is described. The complementary methods relied on stereoselective indium-mediated additions of ethyl α-bromomethyl acrylate to functionalised aldehydes. With an α-hydroxy aldehyde, (2R, 3R)-2,3-dihydroxy-4-oxo butanoic acid dipropylamide, the addition was chelation controlled, and the syn product, (6R, 5R, 4S)-6-dipropylcarbamoyl-2-methylidene-4,5,6-trihydroxy-hexanoic acid ethyl ester, was obtained. In contrast, the stereochemical outcome of the addition to (2R, 3A)-N, N-dipropyl-2,3-O-isopropylidene-4-oxobutyramide was consistent with Felkin-Anh control, and the anti adduct, (4R, 5R, 6R)-6-dipropylcarbamoyl-2- methylidene-4-hydroxy-5,6-O-isopropylidene-hexanoic acid ethyl ester, was the major product. Ozonolysis and deprotection gave the screening substrates as mixtures of furanose and pyranose forms, in good yields. The Royal Society of Chemistry 2005.
An unusual acetonide group migration
Saksena, Anil K.,Girijavallabhan, Viyyoor M.,Puar, Mohindar S.,Pramanik, Birendra N.,Das, Pradip R.,McPhail, Andrew T.
, p. 7201 - 7204 (2007/10/03)
Treatment of (2S,3R)-2,3-O-isopropyliden-4-penten-1,2,3-triol mesylate with uracil, K2CO3 did not provide the product of S N2 displacement, but an interesting acetonide group migration product 8. The structure of 8 was secured by spectral analysis and single crystal X-ray analysis. The desired product 2 could be ultimately obtained by Mitsunobu reaction of the alcohol 6 with 3-N-benzoyl uracil followed by basic hydrolysis.
From Carbohydrates to Carbocycles: Radical Routes via Tellurium Derivatives
Barton, Derek H. R.,Camara, Jose,Cheng, Xiaoqin,Gero, Stephane D.,Jaszberenyi, Joseph Cs.,Quiclet-Sire, Beatrice
, p. 9261 - 9276 (2007/10/02)
D-Ribose was transformed to its protected tosylate 15, followed by a Wittig-reaction to give 16 as a 3:1 mixture of the corresponding Z and E isomers.This mixture was then transformed to the anisyltelluride 17 and the latter cyclized in a radical exchange reaction to a mixture of the carbocycles 18a and 18b (in a 17:2 ratio).The major product 18a was then transformed to various chiral cyclopentane derivatives including the cyclopentenone-derivative 23.Various other carbohydrate-based approaches have also been explored.
Highly Selective Metal-Graphite-Induced Reductions of Deoxy Halo Sugars
Fuerstner, Alois,Weidmann, Hans
, p. 2307 - 2311 (2007/10/02)
To explore the applicability of highly active metal-graphite reducing agents to polyfunctional compounds a variety of suitably protected chloro-, bromodeoxy-, and deoxyiodohexopyranosides and hexofuranoses were each treated with potassium-graphite laminat
Synthesis of Optically Active Olefinic Building Blocks from D-Ribonolactone: Isopropylidene Derivatives of D-erythro-Pentenediol and -triol (cis-4-Substituted 5-Vinyldioxolanes)
Jaeger, Volker,Haefele, Brigitte
, p. 801 - 806 (2007/10/02)
Optically active D-erythro-pentenediol and triol acetonides 4-11 were prepared from D-ribonolactone 1, via the acid 4 and the alcohol 9 as key intermediates.Acetonides 4-11 are cis-4-substituted 5-vinyldioxolanes, both needed as standard model substrates
