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Literature DB >> 16433500

Total synthesis of garsubellin A.

Dionicio R Siegel¹, Samuel J Danishefsky.

Abstract

A concise approach to the laboratory synthesis of garsubellin A is described. Garsubellin A, an effective inducer of choline acetyltransferase (ChAT), has been shown to have potential as a therapeutic agent for the treatment of Alzheimer's disease. Starting from 3,5-dimethoxyphenol, the synthesis has provided garsubellin A in an 18-step sequence. Notable transformations include dearomative allylation, diastereoselective vinylogous lactonization, iodocarbocyclization, transannular Wurtz, and bridgehead functionalization reactions.

Entities: Chemical Disease Species

Mesh：

Substances：
Terpenes
garsubellin A

Year: 2006 PMID： 16433500 DOI： 10.1021/ja057418n

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

16 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: total synthesis of (+/-)-clusianone(1).

Authors: Ji Qi; John A Porco
Journal: J Am Chem Soc Date: 2007-09-29 Impact factor: 15.419

10. Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors: Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal: Tetrahedron Date: 2008-01-28 Impact factor: 2.457

Total synthesis of garsubellin A.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: total synthesis of (+/-)-clusianone(1).

3. Total synthesis of (±)-7-epi-nemorosone.

4. Electrophilic aromatic prenylation via cascade cyclization.

5. The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A.

6. Progress towards the synthesis of Papuaforin A: Selective formation of α-bromoenones from silyl enol ethers.

7. Total synthesis of plukenetione A.

8. Catalytic enantioselective claisen rearrangements of O-allyl β-ketoesters.

Review 9. Dearomatization strategies in the synthesis of complex natural products.

10. Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.