Total Synthesis of Garsubellin A

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2006 Jan 26

PMID 16433500

Citations 22

Authors

Dionicio R Siegel

Samuel J Danishefsky

Affiliations

Soon will be listed here.

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.

Citing Articles

Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates.

Nair D, Tiwari A, Laha B, Namboothiri I Beilstein J Org Chem. 2024; 20:2016-2023.

PMID: 39161707 PMC: 11331540. DOI: 10.3762/bjoc.20.177.

Total Synthesis of Hypersampsone M.

Samkian A, Virgil S, Stoltz B J Am Chem Soc. 2024; 146(28):18886-18891.

PMID: 38958271 PMC: 11258692. DOI: 10.1021/jacs.4c07007.

Neurotrophic Natural Products.

Fukuyama Y, Kubo M, Harada K Prog Chem Org Nat Prod. 2024; 123:1-473.

PMID: 38340248 DOI: 10.1007/978-3-031-42422-9_1.

Different routes for the construction of biologically active diversely functionalized bicyclo[3.3.1]nonanes: an exploration of new perspectives for anticancer chemotherapeutics.

Roy N, Das R, Paira R, Paira P RSC Adv. 2023; 13(32):22389-22480.

PMID: 37501776 PMC: 10369265. DOI: 10.1039/d3ra02003g.

Enantioselective Total Synthesis of (+)-Garsubellin A.

Jang D, Choi M, Chen J, Lee C Angew Chem Int Ed Engl. 2021; 60(42):22735-22739.

PMID: 34398517 PMC: 8519110. DOI: 10.1002/anie.202109193.