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Literature DB >> 24058268

Total Synthesis of (±)-Dragmacidin E: Problems Solved and Lessons Learned.

Abstract

(±)-Dragmacidin E was synthesized in 25 steps from commercially available 7-(benzyloxy)indole. Key transformations in this sponge metabolite's preparation include (a) a Witkop cyclization to establish the bridging indole core, (b) cyclo-dehydrative pyrazinone formation to unite the two indole-bearing components, and (c) late-stage guanidine installation via chemoselective carbonyl activation.

Entities: Chemical Disease Species

Keywords: Organic synthesis; Witkop cyclization; alkaloid; and pyrazinone; marine

Year: 2012 PMID： 24058268 PMCID： PMC3779142 DOI： 10.1055/s-0031-1290692

Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454

25 in total

1. Chemistry and biology of diazonamide A: first total synthesis and confirmation of the true structure.

Authors: K C Nicolaou; David Y-K Chen; Xianhai Huang; Taotao Ling; Marco Bella; Scott A Snyder
Journal: J Am Chem Soc Date: 2004-10-13 Impact factor: 15.419

2. Total synthesis of (±)-dragmacidin E.

Authors: Ken S Feldman; Paiboon Ngernmeesri
Journal: Org Lett Date: 2011-09-29 Impact factor: 6.005

3. Total synthesis of (±)-decursivine and (±)-serotobenine: a Witkop photocyclization/elimination/O-Michael addition cascade approach.

Authors: Hua Qin; Zhengren Xu; Yuxin Cui; Yanxing Jia
Journal: Angew Chem Int Ed Engl Date: 2011-04-18 Impact factor: 15.336

4. Dragmacidins: new protein phosphatase inhibitors from a southern australian deep-water marine sponge, spongosorites sp

Authors:
Journal: J Nat Prod Date: 1998-05 Impact factor: 4.050

Total Synthesis of (±)-Dragmacidin E: Problems Solved and Lessons Learned.

1. Chemistry and biology of diazonamide A: first total synthesis and confirmation of the true structure.

2. Total synthesis of (±)-dragmacidin E.

3. Total synthesis of (±)-decursivine and (±)-serotobenine: a Witkop photocyclization/elimination/O-Michael addition cascade approach.

4. Dragmacidins: new protein phosphatase inhibitors from a southern australian deep-water marine sponge, spongosorites sp

5. A stereospecific total synthesis of d,l-saxitoxin.

6. Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment.

Review 7. A unified synthetic approach to the pyrazinone dragmacidins.

8. Dragmacidin E synthesis studies. Preparation of a model heptacyclic core structure.

9. Extending Pummerer reaction chemistry. Synthesis studies in the phakellin alkaloid area.

10. Enantioselective total syntheses of (+)-arborescidine A, (-)-arborescidine B, and (-)-arborescidine C.

1. Syntheses of Cyclic Guanidine-Containing Natural Products.

Review 2. Recent Advances in the Isolation, Synthesis and Biological Activity of Marine Guanidine Alkaloids.