Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Toward the Synthesis of Nuphar Sesquiterpene Thioalkaloids: Stereodivergent Rhodium-Catalyzed Synthesis of the Thiolane Subunit.

Literature DB >> 26147579

Toward the Synthesis of Nuphar Sesquiterpene Thioalkaloids: Stereodivergent Rhodium-Catalyzed Synthesis of the Thiolane Subunit.

Ping Lu¹, Aaron T Herrmann¹, Armen Zakarian¹.

Abstract

A stereodivergent approach to the central thiolane subunit of Nuphar sesquiterpene thioalkaloids has been developed. This approach features a rhodium-catalyzed Stevens-type rearrangement in conjunction with an enzyme resolution reaction. Further elaboration into a polycyclic ring system via alcohol oxidation and ring-closing metathesis is also described.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：

Year: 2015 PMID： 26147579 PMCID： PMC4924923 DOI： 10.1021/acs.joc.5b01177

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

23 in total

Review 1. Enantioselective enzymatic desymmetrizations in organic synthesis.

Authors: Eduardo García-Urdiales; Ignacio Alfonso; Vicente Gotor
Journal: Chem Rev Date: 2005-01 Impact factor: 60.622

Review 2. Cofactor biosynthesis: an organic chemist's treasure trove.

Authors: Tadhg P Begley
Journal: Nat Prod Rep Date: 2006-01-04 Impact factor: 13.423

3. Interplay of direct stereocontrol and dynamic kinetic resolution in a bifunctional amine thiourea catalyzed highly enantioselective cascade Michael-Michael reaction.

Authors: Chenguang Yu; Yinan Zhang; Aiguo Song; Yafei Ji; Wei Wang
Journal: Chemistry Date: 2010-12-15 Impact factor: 5.236

4. Enantioselective organocatalytic double Michael addition reactions.

Authors: Hao Li; Liansuo Zu; Hexin Xie; Jian Wang; Wei Jiang; Wei Wang
Journal: Org Lett Date: 2007-03-21 Impact factor: 6.005

5. Synthesis of (-)-neothiobinupharidine.

Authors: Daniel J Jansen; Ryan A Shenvi
Journal: J Am Chem Soc Date: 2013-01-11 Impact factor: 15.419

6. Anionic, in situ generation of formaldehyde: a very useful and versatile tool in synthesis.

Authors: Geoffrey Deguest; Laurent Bischoff; Corinne Fruit; Francis Marsais
Journal: Org Lett Date: 2007-02-20 Impact factor: 6.005

7. Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions.

Authors: Sven Brandau; Eddy Maerten; Karl Anker Jørgensen
Journal: J Am Chem Soc Date: 2006-11-22 Impact factor: 15.419

8. Nuphar lutea thioalkaloids inhibit the nuclear factor kappaB pathway, potentiate apoptosis and are synergistic with cisplatin and etoposide.

Authors: Janet Ozer; Nadav Eisner; Elena Ostrozhenkova; Adelbert Bacher; Wolfgang Eisenreich; Daniel Benharroch; Avi Golan-Goldhirsh; Jacob Gopas
Journal: Cancer Biol Ther Date: 2009-10 Impact factor: 4.742

Review 5. Recent synthesis of thietanes.

Authors: Jiaxi Xu
Journal: Beilstein J Org Chem Date: 2020-06-22 Impact factor: 2.883

5 in total

Toward the Synthesis of Nuphar Sesquiterpene Thioalkaloids: Stereodivergent Rhodium-Catalyzed Synthesis of the Thiolane Subunit.

Review 1. Enantioselective enzymatic desymmetrizations in organic synthesis.

Review 2. Cofactor biosynthesis: an organic chemist's treasure trove.

3. Interplay of direct stereocontrol and dynamic kinetic resolution in a bifunctional amine thiourea catalyzed highly enantioselective cascade Michael-Michael reaction.

4. Enantioselective organocatalytic double Michael addition reactions.

5. Synthesis of (-)-neothiobinupharidine.

6. Anionic, in situ generation of formaldehyde: a very useful and versatile tool in synthesis.

7. Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions.

8. Nuphar lutea thioalkaloids inhibit the nuclear factor kappaB pathway, potentiate apoptosis and are synergistic with cisplatin and etoposide.

9. Potent anti-metastatic activity of dimeric sesquiterpene thioalkaloids from the rhizome of Nuphar pumilum.

10. Stereoselective synthesis of enantiomerically pure nupharamine alkaloids from castoreum.

1. Natural products as inspiration for the development of new synthetic methods.

2. Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

3. Synthesis and Sulfur Electrophilicity of the Nuphar Thiaspirane Pharmacophore.

Review 4. Sulfur-Based Ylides in Transition-Metal-Catalysed Processes.

Review 5. Recent synthesis of thietanes.