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Literature DB >> 18582046

Enantioselective total synthesis of lycopodine.

Hua Yang¹, Rich G Carter, Lev N Zakharov.

Abstract

The first enantioselective total synthesis of lycopodine has been completed. Key steps include a highly diastereoselective organocatalyzed cyclization of a keto sulfone to establish the key C7 and C8 stereocenters and a tandem 1,3-sulfonyl shift/intramolecular Mannich cyclization to form the tricyclic core.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 18582046 PMCID： PMC2528287 DOI： 10.1021/ja803613w

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

8 in total

Review 1. The Lycopodium alkaloids.

Authors: Jun'ichi Kobayashi; Hiroshi Morita
Journal: Alkaloids Chem Biol Date: 2005

2. Synthesis of the C1-C26 northern portion of azaspiracid-1: kinetic versus thermodynamic control of the formation of the bis-spiroketal.

Authors: Xiao-Ti Zhou; Rich G Carter
Journal: Angew Chem Int Ed Engl Date: 2006-03-03 Impact factor: 15.336

3. The stereospecific total synthesis of dl-lycopodine.

Authors: G Stork; R A Kretchmer; R H Schlessinger
Journal: J Am Chem Soc Date: 1968-03-13 Impact factor: 15.419

4. The synthesis of dl-lycopodine.

Authors: W A Ayer; W R Bowman; T C Joseph; P Smith
Journal: J Am Chem Soc Date: 1968-03-13 Impact factor: 15.419

5. Anticholinesterase activity in an alkaloid extract of Huperzia saururus.

Authors: M G Ortega; A M Agnese; J L Cabrera
Journal: Phytomedicine Date: 2004-09 Impact factor: 5.340

Review 6. The Lycopodium alkaloids.

Authors: Xiaoqiang Ma; David R Gang
Journal: Nat Prod Rep Date: 2004-10-21 Impact factor: 13.423

7. Utilization of the Intramolecular Cycloaddition-Cationic pi-Cyclization of an Isomünchnone Derivative for the Synthesis of (+/-)-Lycopodine.

Authors: Albert Padwa; Michael A. Brodney; Joseph P. Marino; Scott M. Sheehan
Journal: J Org Chem Date: 1997-01-10 Impact factor: 4.354

8. Palladium-catalyzed enantioselective 1,3-rearrangement of racemic allylic sulfinates: asymmetric synthesis of allylic sulfones and kinetic resolution of an allylic sulfinate.

Authors: Thomas Jagusch; Hans-Joachim Gais; Oleg Bondarev
Journal: J Org Chem Date: 2004-04-16 Impact factor: 4.354

8 in total

11 in total

1. Synthesis of (±)-7-hydroxylycopodine.

Authors: Hong-Yu Lin; Barry B Snider
Journal: Org Lett Date: 2011-01-27 Impact factor: 6.005

2. Synthesis of (±)-7-hydroxylycopodine.

Authors: Hong-Yu Lin; Robert Causey; Gregory E Garcia; Barry B Snider
Journal: J Org Chem Date: 2012-03-30 Impact factor: 4.354

3. 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

10. Ligand-Mediated and Copper-Catalyzed C(sp(3))-H Bond Functionalization of Aryl Ketones with Sodium Sulfinates under Mild Conditions.

Authors: Xing-Wang Lan; Nai-Xing Wang; Cui-Bing Bai; Wei Zhang; Yalan Xing; Jia-Long Wen; Yan-Jing Wang; Yi-He Li
Journal: Sci Rep Date: 2015-12-18 Impact factor: 4.379

Enantioselective total synthesis of lycopodine.

Review 1. The Lycopodium alkaloids.

2. Synthesis of the C1-C26 northern portion of azaspiracid-1: kinetic versus thermodynamic control of the formation of the bis-spiroketal.

3. The stereospecific total synthesis of dl-lycopodine.

4. The synthesis of dl-lycopodine.

5. Anticholinesterase activity in an alkaloid extract of Huperzia saururus.

Review 6. The Lycopodium alkaloids.

7. Utilization of the Intramolecular Cycloaddition-Cationic pi-Cyclization of an Isomünchnone Derivative for the Synthesis of (+/-)-Lycopodine.

8. Palladium-catalyzed enantioselective 1,3-rearrangement of racemic allylic sulfinates: asymmetric synthesis of allylic sulfones and kinetic resolution of an allylic sulfinate.

1. Synthesis of (±)-7-hydroxylycopodine.

2. Synthesis of (±)-7-hydroxylycopodine.

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

4. Stereoselective synthesis of the eastern quinolizidine portion of himeradine A.

5. Development of an enantioselective route toward the Lycopodium alkaloids: total synthesis of lycopodine.

6. Pyridone annulation via tandem Curtius rearrangement/6π-electrocyclization: total synthesis of (-)-lyconadin C.

7. Proline Sulfonamide-Based Organocatalysis: Better Late than Never.

8. Total synthesis of the lycopodium alkaloid (+)-serratezomine A.

9. Toward a unified approach for the lycopodines: synthesis of 10-hydroxylycopodine, deacetylpaniculine, and paniculine.

10. Ligand-Mediated and Copper-Catalyzed C(sp(3))-H Bond Functionalization of Aryl Ketones with Sodium Sulfinates under Mild Conditions.