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Stereoselective synthesis of seven-membered lactams and lactones on a carbohydrate scaffold using ring-closing metathesis

✍ Scribed by Dominic L. Laventine; Paul M. Cullis; Marcos D. García; Paul R. Jenkins

Book ID
104096459
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
622 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

We present here the application of Grubbs' 2nd generation catalyst for the ring-closing metathesis of electron-deficient a,b-unsaturated amides and esters leading to the synthesis of enantiopure azepinone and oxepinone derivatives on a carbohydrate glycoside scaffold. The relative stereochemistries of the compounds obtained were corroborated by X-ray crystallography, 1 H NMR or deduced based on previously reported results. These compounds are designed as precursors of new polyhydroxylated heteroannulated sugars with potential biological activity.

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Stereoselective Synthesis of the Natural
Stereoselective Synthesis of the Naturally Occurring Lactones (−)-Osmundalactone and (−)-Muricatacine Using Ring-Closing Metathesis
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The stereoselective synthesis of the naturally occurring lactones osmundalactone (-)-1 and muricatacin (-)-2 is described. The key steps in each synthesis are the stereoselective addition of a Grignard reagent to a suitably protected αhydroxy aldehyde and a ring-closing metathesis.

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The structure of the metathesis catalyst 10 depicted in Scheme 2 on page 2650 is not correct; instead, it should read PhCHϭRuCl 2 (PCy 3 ) 2 (Cy ϭ cyclohexyl).

ChemInform Abstract: Synthesis of Conjug
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## Abstract For the synthesis of a 12‐membered salicylic macrolide scaffold, ring‐closing metathesis (RCM) of a ω‐diene compound was planned. The stereochemical outcome of the RCM reaction changed depending on the type of Ru catalyst that was used; a “first‐generation” Grubbs catalyst produced excl