2011
DOI: 10.1021/ol202140y
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Concise Asymmetric Total Synthesis of 9-epi-Sessilifoliamide J

Abstract: A 10-step asymmetric synthesis of 9-epi-sessilifoliamide J (20), together with sessilifoliamide J (6), has been accomplished from the key chiral building block 11 via a threo-selective vinylogous Mannich reaction and a Ley oxidation-SmI(2)-mediated coupling lactonization. The absolute configuration of the natural sessilifoliamide J was established.

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Cited by 23 publications
(24 citation statements)
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“…Finally, Huang reported the total synthesis of 9‐epi sessilifoliamide J using a SmI 2 ‐mediated reductive coupling of ketone 158 with methyl methacrylate as the final step (Scheme ) . In an alternative protocol, cross‐coupling with β‐bromo‐methacrylate, followed by hydrogenation and lactonization under acidic conditions, gave improved stereocontrol in this transformation.…”
Section: From Aldehydes and Ketonesmentioning
confidence: 99%
“…Finally, Huang reported the total synthesis of 9‐epi sessilifoliamide J using a SmI 2 ‐mediated reductive coupling of ketone 158 with methyl methacrylate as the final step (Scheme ) . In an alternative protocol, cross‐coupling with β‐bromo‐methacrylate, followed by hydrogenation and lactonization under acidic conditions, gave improved stereocontrol in this transformation.…”
Section: From Aldehydes and Ketonesmentioning
confidence: 99%
“…Huang and co-workers took advantage of a diastereoselective VMR for the creation of the tricyclic structure of the stemona alkaloid, 9-epi-sessilifoliamide J (144). 64 The piperidine core was synthesized through the reaction of bicyclic N,O-acetal 141 with 2-methylsilyloxyfuran 142, giving optimum results with TMSOTf as a Lewis acid. VMR adduct 143 was introduced into the synthetic sequence as a diastereoisomeric mixture, allowing the authors to obtain, in four steps, the complex natural product 144 (Scheme 46).…”
Section: Scheme 44 Total Synthesis Of Indolizidine Alkaloids 137a-dmentioning
confidence: 99%
“…In the exploration of an enantioselective synthesis of (-)stemoamide [14], Hong's group employed the asymmetric hydrogenation of alkynone 23 using Noyori's catalyst (24), giving rise to the optically pure alcohol 25 (Scheme 2). Subsequent homologation of 25 provided 26, which could be further converted to the bicyclic 20a/b as a pair of an inseparable mixture (cis/trans 3:1), according to the similar sequence.…”
Section: Stemoamide-typementioning
confidence: 99%
“…Natural Product Communications Vol. 10 (6) 2015Liu & Wang Synthesis of (-)-9-epi-stemoamide by Wipf et al[21].\ Synthesis of (-)-9-epi-sessilifoliamide J by Huang and co-workers[24]. Huang's synthesis of (-)-sessilifoliamide J[25].…”
mentioning
confidence: 99%