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Literature DB >> 18489177

Total synthesis of the Hsp90 inhibitor geldanamycin.

Abstract

An enantioselective synthesis of the Hsp90 inhibitor geldanamycin was achieved in 20 linear steps and 2.0% overall yield from 2-methoxyhydroquinone. The synthesis is highlighted by a regio- and stereoselective hydroboration reaction; a Sc(OTf)(3)/Et(3)SiH-mediated pyran ring-opening reaction; an enantioselective crotylation to simultaneously install the C8-C9 (E) -trisubstituted olefin, the C10 and C11 stereocenters; a chelation-controlled asymmetric metallated acetylide addition; and an intramolecular copper(I)-mediated aryl amidation reaction to close the 19-membered macrolactam.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2008 PMID： 18489177 PMCID： PMC2430885 DOI： 10.1021/ol800749w

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

29 in total

1. A mild method for the preparation of gamma-hydroxy-alpha,beta-acetylenic esters.

Authors: Shatrughan P Shahi; Kazunori Koide
Journal: Angew Chem Int Ed Engl Date: 2004-05-03 Impact factor: 15.336

2. New conjunctive reagents as cross-coupling partners en route to retinoid-like polyenes.

Authors: Bruce H Lipshutz; Giuliano C Clososki; Will Chrisman; David W Chung; David B Ball; Jennifer Howell
Journal: Org Lett Date: 2005-10-13 Impact factor: 6.005

3. Total synthesis of macbecin I.

Authors: Justin K Belardi; Glenn C Micalizio
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

Review 4. Heat-shock protein 90, a chaperone for folding and regulation.

Authors: D Picard
Journal: Cell Mol Life Sci Date: 2002-10 Impact factor: 9.261

5. Geldanamycin. I. Structure assignment.

Authors: K Sasaki; K L Rinehart; G Slomp; M F Grostic; E C Olson
Journal: J Am Chem Soc Date: 1970-12-30 Impact factor: 15.419

6. Mild reductive opening of aryl pyranosides promoted by scandium(III) triflate.

Authors: Hua-Li Qin; Jason T Lowe; James S Panek
Journal: J Am Chem Soc Date: 2007-01-10 Impact factor: 15.419

7. Synthesis and enzyme-specific activation of carbohydrate-geldanamycin conjugates with potent anticancer activity.

Authors: Hao Cheng; Xianhua Cao; Ming Xian; Lanyan Fang; Tingwei Bill Cai; Jacqueline Jia Ji; Josefino B Tunac; Duxin Sun; Peng George Wang
Journal: J Med Chem Date: 2005-01-27 Impact factor: 7.446

8. Total synthesis of (+)-geldanamycin and (-)-o-quinogeldanamycin: asymmetric glycolate aldol reactions and biological evaluation.

Authors: Merritt B Andrus; Erik L Meredith; Erik J Hicken; Bryon L Simmons; Russell R Glancey; Wei Ma
Journal: J Org Chem Date: 2003-10-17 Impact factor: 4.354

Review 9. Clinical development of 17-allylamino, 17-demethoxygeldanamycin.

Authors: Edward A Sausville; Joseph E Tomaszewski; Percy Ivy
Journal: Curr Cancer Drug Targets Date: 2003-10 Impact factor: 3.428

Review 10. Hsp90: a specialized but essential protein-folding tool.

Authors: J C Young; I Moarefi; F U Hartl
Journal: J Cell Biol Date: 2001-07-23 Impact factor: 10.539

16 in total

1. Total synthesis of (+)-isatisine A.

Authors: Jihoon Lee; James S Panek
Journal: Org Lett Date: 2010-12-28 Impact factor: 6.005

2. Reaction design, discovery, and development as a foundation to function-oriented synthesis.

Authors: Glenn C Micalizio; Sarah B Hale
Journal: Acc Chem Res Date: 2015-02-10 Impact factor: 22.384

3. Mccrearamycins A-D, Geldanamycin-Derived Cyclopentenone Macrolactams from an Eastern Kentucky Abandoned Coal Mine Microbe.

Authors: Xiachang Wang; Yinan Zhang; Larissa V Ponomareva; Qingchao Qiu; Ryan Woodcock; Sherif I Elshahawi; Xiabin Chen; Ziyuan Zhou; Bruce E Hatcher; James C Hower; Chang-Guo Zhan; Sean Parkin; Madan K Kharel; S Randal Voss; Khaled A Shaaban; Jon S Thorson
Journal: Angew Chem Int Ed Engl Date: 2017-01-31 Impact factor: 15.336

Total synthesis of the Hsp90 inhibitor geldanamycin.

1. A mild method for the preparation of gamma-hydroxy-alpha,beta-acetylenic esters.

2. New conjunctive reagents as cross-coupling partners en route to retinoid-like polyenes.

3. Total synthesis of macbecin I.

Review 4. Heat-shock protein 90, a chaperone for folding and regulation.

5. Geldanamycin. I. Structure assignment.

6. Mild reductive opening of aryl pyranosides promoted by scandium(III) triflate.

7. Synthesis and enzyme-specific activation of carbohydrate-geldanamycin conjugates with potent anticancer activity.

8. Total synthesis of (+)-geldanamycin and (-)-o-quinogeldanamycin: asymmetric glycolate aldol reactions and biological evaluation.

Review 9. Clinical development of 17-allylamino, 17-demethoxygeldanamycin.

Review 10. Hsp90: a specialized but essential protein-folding tool.

1. Total synthesis of (+)-isatisine A.

2. Reaction design, discovery, and development as a foundation to function-oriented synthesis.

3. Mccrearamycins A-D, Geldanamycin-Derived Cyclopentenone Macrolactams from an Eastern Kentucky Abandoned Coal Mine Microbe.

Review 4. Human telomerase inhibitors from microbial source.

Review 5. Conformation-activity relationships of polyketide natural products.

6. Diamine Ligands in Copper-Catalyzed Reactions.

7. Fixing the Unfixable: The Art of Optimizing Natural Products for Human Medicine.

8. Synthesis of reblastatin, autolytimycin, and non-benzoquinone analogues: potent inhibitors of heat shock protein 90.

9. Olefinic-lactone cyclizations to macrocycles.

Review 10. Natural product inhibitors of Hsp90: potential leads for drug discovery.