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Literature DB >> 17217284

Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade.

Hongjun Zhang¹, Jutatip Boonsombat, Albert Padwa.

Abstract

A new strategy for the synthesis of the Strychnos alkaloid (+/-)-strychnine has been developed and is based on an intramolecular [4 + 2]-cycloaddition/rearrangement cascade of an indolyl-substituted amidofuran. The critical D-ring was assembled by an intramolecular palladium-catalyzed enolate-driven cross-coupling of an N-tethered vinyl iodide. [reaction: see text].

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17217284 PMCID： PMC2587098 DOI： 10.1021/ol062728b

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

30 in total

1. Synthesis of Strychnine.

Authors: Josep Bonjoch; Daniel Solé
Journal: Chem Rev Date: 2000-09-15 Impact factor: 60.622

2. Palladium-catalyzed intramolecular coupling of vinyl halides and ketone enolates. Synthesis Of bridged azabicyclic compounds

Authors:
Journal: Org Lett Date: 2000-07-27 Impact factor: 6.005

3. A concise formal total synthesis of (+/-)-strychnine by using a transannular inverse-electron-demand Diels-Alder reaction of a [3](1,3)idolo[3](3,6)pyridazinophane.

Authors: Graham J Bodwell; Jiang Li
Journal: Angew Chem Int Ed Engl Date: 2002-09-02 Impact factor: 15.336

4. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1).

Authors: Ahmed F. Abdel-Magid; Kenneth G. Carson; Bruce D. Harris; Cynthia A. Maryanoff; Rekha D. Shah
Journal: J Org Chem Date: 1996-05-31 Impact factor: 4.354

5. Influence of ground-state conformations on the intramolecular amidofuran Diels-Alder reaction.

Authors: Scott K Bur; Stephen M Lynch; Albert Padwa
Journal: Org Lett Date: 2002-02-21 Impact factor: 6.005

6. Enantioselective total synthesis of Wieland-Gumlich aldehyde and (-)-strychnine

Authors:
Journal: Chemistry Date: 2000-02-18 Impact factor: 5.236

7. The formal total synthesis of (+/-)-strychnine via a cobalt-mediated [2 + 2 + 2]cycloaddition.

Authors: M J Eichberg; R L Dorta; K Lamottke; K P Vollhardt
Journal: Org Lett Date: 2000-08-10 Impact factor: 6.005

8. Approaches to the synthesis of (+/-)-strychnine via the cobalt-mediated [2 + 2 + 2] cycloaddition: rapid assembly of a classic framework.

Authors: M J Eichberg; R L Dorta; D B Grotjahn; K Lamottke; M Schmidt; K P Vollhardt
Journal: J Am Chem Soc Date: 2001-09-26 Impact factor: 15.419

9. Biogenetically inspired approach to the Strychnos alkaloids. Concise syntheses of (+/-)-akuammicine and (+/-)-strychnine.

Authors: M Ito; C W Clark; M Mortimore; J B Goh; S F Martin
Journal: J Am Chem Soc Date: 2001-08-22 Impact factor: 15.419

10. Total synthesis of (+/-)-stenine using the IMDAF cycloaddition of a 2-methylthio-5-amido-substituted furan.

Authors: John D Ginn; Albert Padwa
Journal: Org Lett Date: 2002-05-02 Impact factor: 6.005

6 in total

Review 1. Is there no end to the total syntheses of strychnine? Lessons learned in strategy and tactics in total synthesis.

Authors: Jeffrey S Cannon; Larry E Overman
Journal: Angew Chem Int Ed Engl Date: 2012-03-19 Impact factor: 15.336

Review 2. Dearomatization strategies in the synthesis of complex natural products.

Authors: Stéphane P Roche; John A Porco
Journal: Angew Chem Int Ed Engl Date: 2011-04-19 Impact factor: 15.336

3. "For Its Size, the Most Complex Natural Product Known." Who Deserves Credit for Determining the Structure of Strychnine?

Authors: Jeffrey I Seeman; Mark C House
Journal: ACS Cent Sci Date: 2022-06-08 Impact factor: 18.728