Total synthesis of himandravine.
[reaction: see text] The first total synthesis of (+)-himandravine (1) is described, starting from (2S,6S)-cis-2-formyl-6-methyl-N-Boc-piperidine (8) in 11 linear steps and 17% overall yield. The key step involves a highly diastereoselective intramolecular Diels-Alder reaction of the key intermediate 5 that contains the entire latent carbon framework and functional group substitution of himandravine.
Chackalamannil
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P. M. Gross Chemistry Laboratory, Duke University, Durham, North Carolina 27708-0346, USA.
Davies
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McPhail
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D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D010936:Plant Extracts / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D010880:Piperidines; D010936:Plant Extracts; C438970:himandravine