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Stereoselective synthesis of C15C24 and C25C30 fragments of dolabelides

✍ Scribed by Nicolas Desroy; Rémi Le Roux; Phannarath Phansavath; Lucia Chiummiento; Carlo Bonini; Jean-Pierre Genêt

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
106 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The stereocontrolled synthesis of a C15 C24 fragment of dolabelides is reported. The C19 and C21 hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenations of cyclic hemiketal 4 and b-keto ester 7. The C25 C30 portion of dolabelides was prepared as well by ring opening of chiral epoxy alcohol 12 to set up the C27 stereogenic center.

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