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Literature DB >> 19847335

Recent applications of intramolecular Diels-Alder reactions to natural product synthesis.

Abstract

This tutorial review presents some recent examples of intramolecular Diels-Alder (IMDA) reactions as key complexity-generating steps in the total synthesis of structurally intricate natural products. The opportunities afforded by transannular (TADA) versions of the IMDA reaction in complex molecule assembly are also highlighted. The review is aimed at a wide audience, ranging from advanced undergraduates to seasoned practitioners of total synthesis; since this is an educational overview, only selected highlights from the period 2000-2009 are presented, along with chosen references to other, more comprehensive, reviews.

Mesh：

Substances：
Biological Products

Year: 2009 PMID： 19847335 DOI： 10.1039/b816703f

Source DB: PubMed Journal: Chem Soc Rev ISSN： 0306-0012 Impact factor: 54.564

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Cited

31 in total

10. Enantioselective total synthesis of the reported structures of (-)-9-epi-presilphiperfolan-1-ol and (-)-presilphiperfolan-1-ol: structural confirmation and reassignment and biosynthetic insights.

Authors: Allen Y Hong; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2012-08-22 Impact factor: 15.336

Recent applications of intramolecular Diels-Alder reactions to natural product synthesis.

Review 1. Neurotrophic natural products: chemistry and biology.

2. Synthesis of Polycyclic Nitrogen Heterocycles via Cascade Pd-Catalyzed Alkene Carboamination/Diels-Alder Reactions.

3. Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.

4. Nature-inspired total synthesis of (-)-fusarisetin A.

5. The Intramolecular Diels-Alder Reaction of Tryptamine-Derived Zincke Aldehydes Is a Stepwise Process.

Review 6. Recent advances of Diels-Alderases involved in natural product biosynthesis.

7. Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

8. Fusarisetin A: Scalable Total Synthesis and Related Studies.

9. Synthetic Strategies Toward the Decalin Motif of Maklamicin and Related Spirotetronates.

10. Enantioselective total synthesis of the reported structures of (-)-9-epi-presilphiperfolan-1-ol and (-)-presilphiperfolan-1-ol: structural confirmation and reassignment and biosynthetic insights.