Journal ArticleDOI
A general asymmetric route to trans- or cis-2,6-disubstituted piperidine. First total synthesis of (+)-9-epi-6-epipinidinol and (−)-pinidinol
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In this paper, two AD reactions in a stepwise manner lead to the anti-1,5-diol and syn 1,5diol stereodivergently, which have been converted by aminocyclization into trans and cis -2,6-disubstituted piperidines (trans - and cis-12 ), respectively.About:
This article is published in Tetrahedron.The article was published on 1998-10-29. It has received 35 citations till now. The article focuses on the topics: Total synthesis & Piperidine.read more
Citations
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Syntheses of the sedum and related alkaloids
Roderick W. Bates,Kanicha Sa-ei +1 more
Journal ArticleDOI
Formation of macrocycles via ring-closing olefin metathesis.
Choon Woo Lee,Robert H. Grubbs +1 more
TL;DR: The enhanced metathesis activity of 1,3-dimesityl-4,5-dihydroimidazole-2-ylidene ruthenium carbene catalyst 3 significantly increases the feasibility of synthesizing macrocyclic compounds.
Journal ArticleDOI
A diastereoselective intramolecular hydroamination approach to the syntheses of (+)-, (+/-)-, and (-)-pinidinol.
TL;DR: It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation.
Journal ArticleDOI
N‐Sulfinyl Amines as a Nitrogen Source in the Asymmetric Intramolecular Aza‐Michael Reaction: Total Synthesis of (−)‐Pinidinol
Santos Fustero,Silvia Monteagudo,María Sánchez-Roselló,Sonia Flores,Pablo Barrio,Carlos del Pozo +5 more
TL;DR: N-Sulfinyl amines have been successfully employed as nitrogen nucleophiles for the asymmetric intramolecular aza-Michael reaction and the developed methodology allows access to chiral substituted pyrrolidines and piperidines bearing one or two stereocenters.
Journal ArticleDOI
Asymmetric Synthesis of Acyclic 1,3-Amino Alcohols by Reduction of N-Sulfinyl β-Amino Ketones. Formal Synthesis of (−)-Pinidinol and (+)- Epipinidinol†
TL;DR: A formal asymmetric synthesis of the hydroxy piperidine alkaloids (-)-pinid inol and (+)-epipinidinol from a common N-sulfinyl beta-amino ketone ketal precursor was developed.
References
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Journal ArticleDOI
Catalytic Asymmetric Dihydroxylation
BookDOI
Alkaloids : chemical and biological perspectives
TL;DR: In this paper, the total synthesis of amaryllidaceae alkaloids has been studied using radical cyclization reactions in total syntheses of naturally occurring indole alkaloid.
Journal ArticleDOI
A simplified procedure for the stereospecific transformation of 1,2-diols into epoxides
TL;DR: In this article, a simple, "one-pot" procedure for the conversion of vicinal diols into epoxides via halohydrin ester intermediates has been developed.
Journal ArticleDOI
A Novel Asymmetric Route to Chiral, Nonracemic cis-2,6-Disubstituted Piperidines. Synthesis of (+)-Pinidinone and (+)-Monomorine
Journal ArticleDOI
Absolute configuration of the solenopsins, venom alkaloids of the fire ants
Sabine Leclercq,Isabelle Thirionet,Fabienne Broeders,Désiré Daloze,R. K. Vander Meer,Jean Claude Braekman +5 more
TL;DR: In this article, an effective and practical procedure has been developed that allows the assignment of the absolute configuration of solenopsins from diverse origins to be assigned to a set of different origins.