171622-74-5Relevant academic research and scientific papers
Correction to: Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H (Organic Letters (2016) 18: 15 (3886-3889) DOI: 10.1021/acs.orglett.6b
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supporting information, p. 5186 - 5187 (2016/10/18)
The wrong enantiomers of (?)-gabosine H (5), (?)-epigabosine H (epi-5) and intermediates 6?10, 11a,b, and 12?22 were drawn in the Abstract, Table of Contents, and Schemes 2?6. The correct structural drawings for these compounds are provided. The corrected
Synthesis of exo-methylenedifluorocyclopentanes as precursors of fluorinated carbasugars by 5-exo-dig radical cyclization
Fourrire, Ga?lle,Leclerc, Eric,Quirion, Jean-Charles,Pannecoucke, Xavier
scheme or table, p. 172 - 179 (2012/03/08)
The synthesis of polyhydroxylated 1,1-difluoro-5-methylenecyclopentanes is described. The sequence involves an addition of PhSeCF2TMS to a tartrate-derived aldehyde or its corresponding tert-butanesulfinylimines followed by a radical cyclization. The use of a benzyl protected substrate led to an unproductive 1,5-hydrogen transfer after cyclization but the desired compound was eventually obtained from the unprotected substrate. A hydroboration/oxidation sequence was investigated on these 1,1-difluoro-5- methylenecyclopentanes as it would provide fluorinated carbasugars, a new and promising class of glycomimetics. Unfortunately, this reaction was poorly efficient and its regioselectivity not the expected one.
Synthesis and activity of two trifluorinated analogues of 1-deoxy-d-xylulose 5-phosphate
Meyer, Odile,Grosdemange-Billiard, Catherine,Tritsch, Denis,Rohmer, Michel
, p. 711 - 714 (2007/10/03)
An improved synthesis of 1,1,1-trifluoro-1-deoxy-d-xylulose 5-phosphate and an access to the reduced diastereomer mixture analogues 1,1,1-trifluoro-1-deoxy-d-xylitol 5-phosphate and 1,1,1-trifluoro-1-deoxy-d-lyxitol 5-phosphate are described. Inhibitor ac
Highly stereocontrolled total synthesis of (+)-bengamide E
Mukai, Chisato,Moharram, Sameh M.,Kataoka, Osamu,Hanaoka, Miyoji
, p. 2849 - 2854 (2007/10/02)
Diisopropyl D-tartrate 7 was efficiently transformed into the hexacarbonyl dicobalt complexed aldehyde 23.A highly stereocontrolled aldol reaction of 23 with the O,S-acetal 20 in the presence of tin(IV) chloride provided, after decomplexation, the aldol adduct 21 as the sole product, which was subsequently converted into (+)-bengamide E 5.
An Efficient Method for the Optical Resolution of 3-Hydroxy-2-substituted-4-alkynoates: A Highly Stereoselective Total Synthesis of (+)-Bengamide E
Mukai, Chisato,Kataoka, Osamu,Hanaoka, Miyoji
, p. 5910 - 5918 (2007/10/03)
A novel procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation.Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.
A cobalt-complexed propyanl in organic synthesis: A highly stereoselective total synthesis of bengamide E
Mukai, Chisato,Kataoka, Osamu,Hanaoka, Miyoji
, p. 6899 - 6902 (2007/10/02)
A highly stereoselective aldol reaction of the cobalt-complexed 4-methylpent-2-ynal 2 with O-silyl ketene O,S-acetal 3 provided the syn-aldol product, which was subsequently converted to (+)-bengamide E through optical resolution and the second diastereoselective aldol reaction as crucial steps.
