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Literature DB >> 21879704

Three-component coupling approach to trachyspic acid.

Daniel C Schmitt¹, Leighann Lam, Jeffrey S Johnson.

Abstract

Three-component coupling of the lithium enolate of t-BuOAc, silyl glyoxylate, and an α,β-unsaturated ketone enables the rapid construction of the trachyspic acid carbon skeleton. A 3,4-disubstituted isoxazole is utilized to mask the C7/C9 dicarbonyl. New enolsilane/nitrile-oxide cycloadditions enable the preparation of various 3,4-disubstituted isoxazoles that are challenging to access by other means.

Entities: Chemical Disease Species

Mesh：

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Year: 2011 PMID： 21879704 PMCID： PMC3184321 DOI： 10.1021/ol202002r

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

13 in total

1. Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor.

Authors: Steven C Zammit; Vito Ferro; Edward Hammond; Mark A Rizzacasa
Journal: Org Biomol Chem Date: 2007-07-26 Impact factor: 3.876

2. Redox economy in organic synthesis.

Authors: Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

3. Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.

Authors: Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2010-11-18 Impact factor: 15.419

4. Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures.

Authors: Jeffrey W Bode; Yoshifumi Hachisu; Tomoo Matsuura; Keisuke Suzuki
Journal: Org Lett Date: 2003-02-20 Impact factor: 6.005

5. Three-component coupling reactions of silylglyoxylates, alkynes, and aldehydes: a chemoselective one-step glycolate aldol construction.

Authors: David A Nicewicz; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2005-05-04 Impact factor: 15.419

6. Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

Authors: Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal: Org Lett Date: 2011-05-17 Impact factor: 6.005

7. Enantiospecific synthesis of (-)-trachyspic acid.

Authors: Steven C Zammit; Jonathan M White; Mark A Rizzacasa
Journal: Org Biomol Chem Date: 2005-05-06 Impact factor: 3.876

8. Three-component coupling reactions of silyl glyoxylates, vinyl Grignard reagent, and nitroalkenes: an efficient, highly diastereoselective approach to nitrocyclopentanols.

Authors: Gregory R Boyce; Jeffrey S Johnson
Journal: Angew Chem Int Ed Engl Date: 2010-11-15 Impact factor: 15.336

9. Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction.

Authors: Stephen N Greszler; Jeffrey S Johnson
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

Three-component coupling approach to trachyspic acid.

1. Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor.

2. Redox economy in organic synthesis.

3. Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.

4. Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures.

5. Three-component coupling reactions of silylglyoxylates, alkynes, and aldehydes: a chemoselective one-step glycolate aldol construction.

6. Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

7. Enantiospecific synthesis of (-)-trachyspic acid.

8. Three-component coupling reactions of silyl glyoxylates, vinyl Grignard reagent, and nitroalkenes: an efficient, highly diastereoselective approach to nitrocyclopentanols.

9. Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction.

10. Total synthesis of (+/-)-trachyspic acid and determination of the relative configuration.

1. Three-component glycolate Michael reactions of enolates, silyl glyoxylates, and α,β-enones.

2. Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.

3. Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

4. Alternaric acid: formal synthesis and related studies.