Enantio- and diastereoselective allylmetalations: an easy and efficient access to the AB spiroketal of spongistatin.
[reaction: see text] A unique combination of highly enantio- and diastereoselective allylmetalations and a one-pot "desacetalization/spiroketalization" have been employed to synthesize the AB spiroketal fragment (C1-C13) of spongistatin in 15 steps and in excellent diastereoselectivity.
Allais
Florent
F
Laboratoire de Chimie Organique, Associé au CNRS, ESPCI, 10 rue Vauquelin, F-75231 Paris Cedex 05, France.
Cossy
Janine
J
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
D000970:Antineoplastic Agents; D018942:Macrolides; C083856:spongistatin 1; D000095702:Polyether Toxins