doi: 10.1021/ol060083+.
Total synthesis of the marine alkaloid (+/-)-lepadiformine via a radical carboazidation
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- PMID: 16597112
- DOI: 10.1021/ol060083+
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Total synthesis of the marine alkaloid (+/-)-lepadiformine via a radical carboazidation
Org Lett.
.
Abstract
[reaction: see text] The total synthesis of lepadiformine has been achieved in 10 steps and 15% overall yield from cyclohexanone. The amino-substituted quaternary carbon center is created through a radical carboazidation reaction. The tricyclic core of lepadiformine is built via an efficient hydrogenation process, involving reduction of the azide and intramolecular reductive amination of a ketone, followed by lactamization of the intermediate gamma-aminoester. The hydroxymethyl side chain is introduced according to a modified Takahata procedure after conversion of the lactam into a thiolactam.
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