Concise synthesis of the neo-clerodane skeleton of teucrolivin A using a pericyclic reaction cascade.
Herein, we describe the synthesis of advanced intermediate 39 on the path towards the total synthesis of teucrolivin A (3) in 16 steps from commercially available 1,3-cyclohexadiene. We have constructed the trans-decalin core of the natural product 3 as a single diastereomer using a tandem oxy-Cope/Claisen/ene cascade and in doing so have incorporated sufficient functionality to allow completion of the total synthesis.
Arns
Steve
S
Department of Chemistry, 10 Marie-Curie, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5.
Barriault
Louis
L
D045785:Diterpenes, Clerodane / Q000138:chemical synthesis*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D012821:Silanes / Q000138:chemical synthesis*
C516069:2-furan-3-yl-2-methoxy-3a,4-dimethyl-8-triethylsilanyloxy-3,3a,4,5,9,10-hexahydro-2H,8H-1-oxacyclopenta(d)naphthalen-6-one; D045785:Diterpenes, Clerodane; D006575:Heterocyclic Compounds, 3-Ring; D012821:Silanes; C516070:teucrolivin A