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Total Synthesis of Leiocarpin C and (+)-Goniodiol via an Olefin Cross-Metathesis Protocol

โœ Scribed by Palakodety Radha Krishna; Munagala Alivelu

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
172 KB
Volume
94
Category
Article
ISSN
0018-019X

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โœฆ Synopsis

A stereoselective total synthesis of leiocarpin C ( 2) and (รพ)-Goniodiol (1) by applying olefin crossmetathesis and substrate directed dihydroxylation as the key steps is reported (Scheme 3).

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Short, stereoselective synthesis of C-gl
Short, stereoselective synthesis of C-glycosyl asparagines via an olefin cross-metathesis
โœ Ernest G Nolen; Adam J Kurish; Kelli A Wong; Michael D Orlando ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 321 KB

The Grubbs second generation ruthenium catalyst was employed for the cross metathesis between aand b-C-allyl glycosides and suitably protected L-vinyl glycines to furnish olefinic products in 57-94% yields. Hydrogenation afforded the C-glycosyl asparagines in high yield.