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Glucal

About: Glucal is a research topic. Over the lifetime, 590 publications have been published within this topic receiving 8960 citations. The topic is also known as: D-glucal.


Papers
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Journal ArticleDOI
TL;DR: A convergent total synthesis of 16-membered macrolactone natural product (−)-A26771B 1 starting from 3,4,6-tri-O-acetyl-D-glucal 7 is reported in this paper.
Abstract: A convergent total synthesis of a 16-membered macrolactone natural product (−)-A26771B 1 starting from 3,4,6-tri-O-acetyl-D-glucal 7 is reported. The Ferrier rearrangement of acetylated glucal 7, cross metathesis between chiral fragments 3 and 4, Yamaguchi macrolactonization and selective oxidation of the allylic alcohol are the key features of the synthesis.

20 citations

Journal ArticleDOI
TL;DR: In this article, triphenylphosphane hydrobromide was used as a catalyst for N-N bond formation in dichloromethane or THF, with the first use of HY zeolite to promote theFerrier rearrangement.

20 citations

Journal ArticleDOI
TL;DR: Methyl N-acetyl-α-D-lividosaminide has been synthesized starting from 4,6-di-O-benzyl-Dglucal via a new nitro glucal derivative in six steps as mentioned in this paper.

20 citations

Journal ArticleDOI
TL;DR: Biological evaluation of one migrastatin and one dorrigocin A sugar derived analogue show that they inhibit proliferation and serum-induced migration of tumour and synovial cells at higher concentrations than evodiamine.
Abstract: The synthesis of a range of analogues of the migrastatin macrolide core has been achieved from tri-O-acetyl-D-glucal in order to facilitate structure-activity studies. Efficient macrolactone formation was achieved in the presence of a reactive olefin, by increasing steric hindrance in the olefin environment. Acyclic analogues of migrastatin, structurally related to dorrigocin A, have also been prepared from D-glucal. The dorrigocin A analogues were prepared using the combination of the cross metathesis of ethyl 6-heptenoate with a glycal derivative and a subsequent allylic rearrangement-alkene isomerisation reaction (Perlin reaction). A synthetic route is thus provided that will enable dorrigocin A analogues to be prepared in parallel to migrastatin analogues in the search for novel anti-cancer and anti-arthritic therapeutics. Biological evaluation of one migrastatin and one dorrigocin A sugar derived analogue show that they inhibit proliferation and serum-induced migration of tumour and synovial cells at higher concentrations than evodiamine. Dorrigocin A analogues displayed similar potency to analogues of the migrastatin core.

20 citations

Journal ArticleDOI
TL;DR: The treatment of 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabino-hex-1-enitol with azidotrimethylsilane by the aid of a catalytic amount of Yb(OTf).

20 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20233
20224
20212
20204
20193
20186