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Literature DB >> 17305397

Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine.

Abstract

Sulfinimine-derived N-sulfinyl delta-amino beta-ketophosphonates are transformed via the enaminones to the phosphoryl dihydropyridones that selectively give trans-2,6-disubstituted 1,2,5,6-tetrahydropyridines on organocuprate addition and dephosphorylation.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17305397 PMCID： PMC2597462 DOI： 10.1021/jo062365t

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

27 in total

Review 1. Indolizidine and quinolizidine alkaloids.

Authors: J P Michael
Journal: Nat Prod Rep Date: 2000-12 Impact factor: 13.423

2. A diastereoselective synthesis of 2,4-disubstituted piperidines: scaffolds for drug discovery.

Authors: P S Watson; B Jiang; B Scott
Journal: Org Lett Date: 2000-11-16 Impact factor: 6.005

Review 3. Indolizidine and quinolizidine alkaloids.

Authors: J P Michael
Journal: Nat Prod Rep Date: 2001-10 Impact factor: 13.423

4. A novel C(2)-symmetric 2,6-diallylpiperidine carboxylic acid methyl ester as a promising chiral building block for piperidine-related alkaloids.

Authors: Hiroki Takahata; Hidekazu Ouchi; Motohiro Ichinose; Hideo Nemoto
Journal: Org Lett Date: 2002-10-03 Impact factor: 6.005

5. Synthesis of (--)-lasubine(I) via a planar chiral [(eta6-arene)Cr(CO)3] complex.

Authors: H Ratni; E P Kündig
Journal: Org Lett Date: 1999-12-16 Impact factor: 6.005

6. Synthesis of the quinolizidine alkaloids (-)-lasubine II and (+/-)-myrtine by conjugate addition and intramolecular acylation of amino esters with acetylenic sulfones.

Authors: Thomas G Back; Michael D Hamilton; Vania J J Lim; Masood Parvez
Journal: J Org Chem Date: 2005-02-04 Impact factor: 4.354

7. Addition of metallo enolates to chiral 1-acylpyridinium salts: total synthesis of (+)-cannabisativine.

Authors: J T Kuethe; D L Comins
Journal: Org Lett Date: 2000-03-23 Impact factor: 6.005

8. Novel cyclic sugar imines: carbohydrate mimics and easily elaborated scaffolds for aza-sugars.

Authors: Benjamin G Davis; Michael A T Maughan; Timothy M Chapman; Renaud Villard; Steve Courtney
Journal: Org Lett Date: 2002-01-10 Impact factor: 6.005

9. Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived delta-lactam.

Authors: Mercedes Amat; Núria Llor; José Hidalgo; Carmen Escolano; Joan Bosch
Journal: J Org Chem Date: 2003-03-07 Impact factor: 4.354

10. Asymmetric synthesis of cis-5-substituted pyrrolidine 2-phosphonates using metal carbenoid NH insertion and delta-amino beta-ketophosphonates.

Authors: Franklin A Davis; Yongzhong Wu; He Xu; Junyi Zhang
Journal: Org Lett Date: 2004-11-25 Impact factor: 6.005

8 in total

1. Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.

Authors: Nagarathanam Veerasamy; Erik C Carlson; Nathan D Collett; Mrinmoy Saha; Rich G Carter
Journal: J Org Chem Date: 2013-04-29 Impact factor: 4.354

2. Sulfinimine-derived 2,3-diamino esters in the asymmetric synthesis of piperidine (2S,3S)-(+)-CP-99,994.

Authors: Franklin A Davis; Yanfeng Zhang; Danyang Li
Journal: Tetrahedron Lett Date: 2007-10-29 Impact factor: 2.415

3. Palladium-catalyzed direct C-H arylation of cyclic enaminones with aryl iodides.

Authors: Yi-Yun Yu; Lei Bi; Gunda I Georg
Journal: J Org Chem Date: 2013-06-10 Impact factor: 4.354

4. Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes.

Authors: Yi-Yun Yu; Gunda I Georg
Journal: Adv Synth Catal Date: 2014-04-14 Impact factor: 5.837