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Literature DB >> 10808435

Total synthesis of (+/-)-aspidospermidine.

Abstract

(+/-)-Aspidospermidine (1) has been synthesized from readily available methyl 3-ethyl-2-oxocylo-pentanecarboxylate (17) in 5.9% yield over 13 steps. The key step of the synthesis is an intramolecular cascade reaction that simultaneously forms the B, C, and D rings of 1. A high-yielding method of closing the remaining E ring is also described.

Entities: Chemical

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Year: 2000 PMID： 10808435 DOI： 10.1021/jo991599s

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

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Cited

8 in total

Review 1. Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.

Authors: Beau P Pritchett; Brian M Stoltz
Journal: Nat Prod Rep Date: 2018-06-20 Impact factor: 13.423

2. Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

Authors: José M Mejía-Oneto; Albert Padwa
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

3. Formal synthesis of aspidosperma alkaloids via the intramolecular [3 + 2] cycloaddition of 2-azapentdienyllithiums.

Authors: William H Pearson; Aaron Aponick
Journal: Org Lett Date: 2006-04-13 Impact factor: 6.005

4. Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.

Authors: Rajesh Iyengar; Klaas Schildknegt; Martha Morton; Jeffrey Aubé
Journal: J Org Chem Date: 2005-12-23 Impact factor: 4.354

Total synthesis of (+/-)-aspidospermidine.

Review 1. Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.

2. Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

3. Formal synthesis of aspidosperma alkaloids via the intramolecular [3 + 2] cycloaddition of 2-azapentdienyllithiums.

4. Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.

5. A model study toward the total synthesis of N-deacetyllappaconitine.

6. A Dipolar Cycloaddition Approach Toward the Kopsifoline Alkaloid Framework.

7. Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3 + 2] annulation.

8. A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.