Total asymmetric synthesis of the aphidicolin derivative (11R)-(-)-8-epi-11-hydroxyaphidicolin using tandem transannular Diels-Alder/aldol reactions.
[reaction: see text] Aphidicolin unnatural derivative (2) was synthesized using a new tandem transannular Diels-Alder/aldol methodology. The 8-epi-aphidicolane skeleton is constructed in a highly diastereoselective manner and converted into (11R)-(-)-8-epi-11-hydroxyaphidicolin (2). An efficient method for the difficult C16 funtionalization is presented.
Bélanger
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Laboratoire de synthèse organique, Institut de pharmacologie de Sherbrooke, Université de Sherbrooke, Québec, Canada.
Deslongchamps
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P
D000164:Acremonium / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry; D000998:Antiviral Agents / Q000737:chemistry; D016590:Aphidicolin / Q000031:analogs & derivatives* / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D004224:Diterpenes; D004791:Enzyme Inhibitors; D016590:Aphidicolin