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Literature DB >> 33155164

Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction.

Yuan Huang¹, Fanglin Xue¹, Hengmao Liu¹, Fei Xue¹, Xiao-Yu Liu¹, Hao Song², Yong Qin³.

Abstract

An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visible-light photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement to establish the C20 all-carbon quaternary stereocenter.

Entities: Chemical Disease Gene

Keywords: Eburnamine-vincamine alkaloids; Johnson-claisen rearrangement; Photochemistry; Radical cascade reaction

Year: 2020 PMID： 33155164 DOI： 10.1007/s13659-020-00276-8

Source DB: PubMed Journal: Nat Prod Bioprospect ISSN： 2192-2209

16 in total

1. A short synthesis of (+/-)-eburnamonine.

Authors: A K Ghosh; R Kawahama
Journal: J Org Chem Date: 2000-08-25 Impact factor: 4.354

2. [Stereoselective synthesis of optically active vincamine].

Authors: P Pfäffli; W Oppolzer; R Wenger; H Hauth
Journal: Helv Chim Acta Date: 1975-06-04 Impact factor: 2.164

3. GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS. IV. A SYNTHESIS OF DL-EBURNAMONINE.

Authors: E WENKERT; B WICKBERG
Journal: J Am Chem Soc Date: 1965-04-05 Impact factor: 15.419

Review 4. Recent progress in the chemistry of indole alkaloids and mould metabolites.

Authors: J E Saxton
Journal: Nat Prod Rep Date: 1994-10 Impact factor: 13.423

Review 5. Eburnamine derivatives and the brain.

Authors: Adám Vas; Balázs Gulyás
Journal: Med Res Rev Date: 2005-11 Impact factor: 12.944

6. A new enantioselective total synthesis of natural vincamine via an intramolecular Mannich reaction of an silyl enol ether.

Authors: W Oppolzer; H Hauth; P Pfäffli; R Wenger
Journal: Helv Chim Acta Date: 1977 Impact factor: 2.164

Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction.

1. A short synthesis of (+/-)-eburnamonine.

2. [Stereoselective synthesis of optically active vincamine].

3. GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS. IV. A SYNTHESIS OF DL-EBURNAMONINE.

Review 4. Recent progress in the chemistry of indole alkaloids and mould metabolites.

Review 5. Eburnamine derivatives and the brain.

6. A new enantioselective total synthesis of natural vincamine via an intramolecular Mannich reaction of an silyl enol ether.

7. Letter: A high yield stereospecific total synthesis of vincamine.

Review 8. Evolution and current status of the phytochemistry of nitrogenous compounds.

9. Brain trace element concentration of rats treated with the plant alkaloid, vincamine.

10. Vincamine: a psychogeriatric agent blocking synaptic potentiation in hippocampus.