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Literature DB >> 16092834

Synthesis of the branched C-glycoside substructure of altromycin B.

Abstract

Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b). [reaction: see text]

Entities: Chemical

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Year: 2005 PMID： 16092834 PMCID： PMC1388186 DOI： 10.1021/ol050975u

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

17 in total

1. Convergent Synthesis of Digitoxin: Stereoselective Synthesis and Glycosylation of the Digoxin Trisaccharide Glycal This research was supported by the U.S. National Institutes of Health (CA-59703). F.E.M. also thanks Novartis Pharmaceuticals for unrestricted additional funding (Grant Program for the Support of Academic Research in Synthetic Organic Chemistry).

Authors: Frank E. McDonald; K. Subba Reddy
Journal: Angew Chem Int Ed Engl Date: 2001-10-01 Impact factor: 15.336

Review 2. Applications of tin-containing intermediates to carbohydrate chemistry.

Authors: T B Grindley
Journal: Adv Carbohydr Chem Biochem Date: 1998 Impact factor: 12.200

3. Altromycins, novel pluramycin-like antibiotics. II. Isolation and elucidation of structure.

Authors: G M Brill; J B McAlpine; D N Whittern; A M Buko
Journal: J Antibiot (Tokyo) Date: 1990-03 Impact factor: 2.649

4. Discovery through total synthesis: a retrospective on the himastatin problem.

Authors: T M Kamenecka; S J Danishefsky
Journal: Chemistry Date: 2001-01-05 Impact factor: 5.236

5. A novel reaction for annulation onto alpha,beta-unsaturated ketones: W(CO)(5).L promoted exo- and endo-selective cyclizations of omega-acetylenic silyl enol ethers prepared by 1,4-addition of propargyl malonate to enones.

Authors: N Iwasawa; K Maeyama; H Kusama
Journal: Org Lett Date: 2001-11-29 Impact factor: 6.005

6. A practical synthesis of (+)-discodermolide and analogues: fragment union by complex aldol reactions.

Authors: I Paterson; G J Florence; K Gerlach; J P Scott; N Sereinig
Journal: J Am Chem Soc Date: 2001-10-03 Impact factor: 15.419

7. Interactions of the anticancer antibiotic altromycin B with copper(II), palladium(II) and platinum(II) ions and in vitro activity of the formed complexes.

Authors: Nikolaos Nikolis; Constantinos Methenitis; George Pneumatikakis; Marina M L Fiallo
Journal: J Inorg Biochem Date: 2002-04-10 Impact factor: 4.155

2. Fischer carbene catalysis of alkynol cycloisomerization: application to the synthesis of the altromycin B disaccharide.

Authors: Bonsuk Koo; Frank E McDonald
Journal: Org Lett Date: 2007-03-27 Impact factor: 6.005

3. Crystal structure of (5R)-5-[(1S)-1,2-di-hydroxy-eth-yl]-4-meth-oxy-3-phenyl-2,5-di-hydro-furan-2-one.

Authors: Santosh R Kote; Shankar R Thopate; Sushil K Gupta; Ray J Butcher
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2014-09-30

3 in total

Synthesis of the branched C-glycoside substructure of altromycin B.

Review 2. Applications of tin-containing intermediates to carbohydrate chemistry.

3. Altromycins, novel pluramycin-like antibiotics. II. Isolation and elucidation of structure.

4. Discovery through total synthesis: a retrospective on the himastatin problem.

5. A novel reaction for annulation onto alpha,beta-unsaturated ketones: W(CO)(5).L promoted exo- and endo-selective cyclizations of omega-acetylenic silyl enol ethers prepared by 1,4-addition of propargyl malonate to enones.

6. A practical synthesis of (+)-discodermolide and analogues: fragment union by complex aldol reactions.

7. Interactions of the anticancer antibiotic altromycin B with copper(II), palladium(II) and platinum(II) ions and in vitro activity of the formed complexes.

8. Synthesis of seven-membered ring glycals via endo-selective alkynol cycloisomerization.

9. Photoactivated tungsten hexacarbonyl-catalyzed conversion of alkynols to glycals.

10. Synthesis of both possible isomers of the northwest quadrant of altromycin B.

1. Synthesis of the aglycones of altromycins and kidamycin from a common intermediate.

2. Fischer carbene catalysis of alkynol cycloisomerization: application to the synthesis of the altromycin B disaccharide.

3. Crystal structure of (5R)-5-[(1S)-1,2-di-hydroxy-eth-yl]-4-meth-oxy-3-phenyl-2,5-di-hydro-furan-2-one.