Journal
ORGANIC LETTERS
Volume 16, Issue 3, Pages 688-691Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol4033495
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Funding
- Vertex Pharmaceuticals
- Allergan Foundation
- UC, Irvine
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A synthetic route to the isotwistane core of palhinine lycopodium alkaloids is described. A Morita-Baylis-Hillman/intramolecular Diels-Alder (IMDA) strategy sets the vicinal all-carbon quaternary centers present in this family of natural products. The regioselectivity of the IMDA reaction is dictated by the conditions employed for silyl enol ether formation, with one set of conditions providing the core of cardionine and alternate conditions generating the desired isotwistane core of isopalhinine.
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