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Literature DB >> 29066794

Enantiospecific total synthesis of the squalene synthase inhibitors (-)-CJ-13,982 and its enantiomer from a common intermediate.

Dayna Sturgess¹, Zongjia Chen¹, Jonathan M White¹, Mark A Rizzacasa¹.

Abstract

The total syntheses of both the natural and unnatural enantiomers of the alkyl citrate natural product CJ-13,982 (1) from the common d-ribose-derived acid 6 are described.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2017 PMID： 29066794 DOI： 10.1038/ja.2017.127

Source DB: PubMed Journal: J Antibiot (Tokyo) ISSN： 0021-8820 Impact factor: 2.649

11 in total

1. The squalestatins, novel inhibitors of squalene synthase produced by a species of Phoma. II. Structure elucidation.

Authors: P J Sidebottom; R M Highcock; S J Lane; P A Procopiou; N S Watson
Journal: J Antibiot (Tokyo) Date: 1992-05 Impact factor: 2.649

2. The squalestatins, novel inhibitors of squalene synthase produced by a species of Phoma. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activity.

Authors: M J Dawson; J E Farthing; P S Marshall; R F Middleton; M J O'Neill; A Shuttleworth; C Stylli; R M Tait; P M Taylor; H G Wildman
Journal: J Antibiot (Tokyo) Date: 1992-05 Impact factor: 2.649

3. 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

4. N-isopropylidene-N'-2-nitrobenzenesulfonyl hydrazine, a reagent for reduction of alcohols via the corresponding monoalkyl diazenes.

Authors: Mohammad Movassaghi; Omar K Ahmad
Journal: J Org Chem Date: 2007-02-03 Impact factor: 4.354

Review 5. Total synthesis of alkyl citrate natural products.

Authors: Mark A Rizzacasa; Dayna Sturgess
Journal: Org Biomol Chem Date: 2014-03-07 Impact factor: 3.876

6. Identification and Heterologous Production of a Benzoyl-Primed Tricarboxylic Acid Polyketide Intermediate from the Zaragozic Acid A Biosynthetic Pathway.

Authors: Nicholas Liu; Yiu-Sun Hung; Shu-Shan Gao; Leibniz Hang; Yi Zou; Yit-Heng Chooi; Yi Tang
Journal: Org Lett Date: 2017-06-13 Impact factor: 6.005

Enantiospecific total synthesis of the squalene synthase inhibitors (-)-CJ-13,982 and its enantiomer from a common intermediate.

1. The squalestatins, novel inhibitors of squalene synthase produced by a species of Phoma. II. Structure elucidation.

2. The squalestatins, novel inhibitors of squalene synthase produced by a species of Phoma. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activity.

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

4. N-isopropylidene-N'-2-nitrobenzenesulfonyl hydrazine, a reagent for reduction of alcohols via the corresponding monoalkyl diazenes.

Review 5. Total synthesis of alkyl citrate natural products.

6. Identification and Heterologous Production of a Benzoyl-Primed Tricarboxylic Acid Polyketide Intermediate from the Zaragozic Acid A Biosynthetic Pathway.

7. CJ-13,981 and CJ-13,982, new squalene synthase inhibitors.

8. A general model for selectivity in olefin cross metathesis.

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

10. Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase.

1. In vitro studies of maleidride-forming enzymes.