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Literature DB >> 19968285

Enantioselective synthesis of (+)-cephalostatin 1.

Kevin C Fortner¹, Darryl Kato, Yoshiki Tanaka, Matthew D Shair.

Abstract

This Article describes an enantioselective synthesis of cephalostatin 1. Key steps of this synthesis are a unique methyl group selective allylic oxidation, directed C-H hydroxylation of a sterol at C12, Au(I)-catalyzed 5-endo-dig cyclization, and a kinetic spiroketalization.

Entities: Chemical

Mesh：

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Year: 2010 PMID： 19968285 DOI： 10.1021/ja906996c

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

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Cited

20 in total

1. Chemical synthesis of 7-oxygenated 12α-hydroxy steroid derivatives to enable the biochemical characterization of cytochrome P450 8B1, the oxysterol 12α-hydroxylase enzyme implicated in cardiovascular health and obesity.

Authors: Samuel D Offei; Hadi D Arman; Mirza Oais Baig; Lazaro S Chavez; Carlos A Paladini; Francis K Yoshimoto
Journal: Steroids Date: 2018-11-03 Impact factor: 2.668

2. Natural products reveal cancer cell dependence on oxysterol-binding proteins.

Authors: Anthony W G Burgett; Thomas B Poulsen; Kittikhun Wangkanont; D Ryan Anderson; Chikako Kikuchi; Kousei Shimada; Shuichi Okubo; Kevin C Fortner; Yoshihiro Mimaki; Minpei Kuroda; Jason P Murphy; David J Schwalb; Eugene C Petrella; Ivan Cornella-Taracido; Markus Schirle; John A Tallarico; Matthew D Shair
Journal: Nat Chem Biol Date: 2011-08-07 Impact factor: 15.040

3. Synthesis and evaluation of a fluorescent ritterazine-cephalostatin hybrid.

Authors: Kanduluru Ananda Kumar; James J La Clair; Philip L Fuchs
Journal: Org Lett Date: 2011-09-14 Impact factor: 6.005

4. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

Authors: Kevin Hung; Matthew L Condakes; Luiz F T Novaes; Stephen J Harwood; Takahiro Morikawa; Zhi Yang; Thomas J Maimone
Journal: J Am Chem Soc Date: 2019-02-11 Impact factor: 15.419

5. Ritterostatin G_N 1_N , a Cephalostatin-Ritterazine Bis-steroidal Pyrazine Hybrid, Selectively Targets GRP78.

Authors: Andrew J Ambrose; Evelyne A Santos; Paula C Jimenez; Danilo D Rocha; Diego V Wilke; Paolo Beuzer; Josh Axelrod; Ananda Kumar Kanduluru; Philip L Fuchs; Hu Cang; Letícia V Costa-Lotufo; Eli Chapman; James J La Clair
Journal: Chembiochem Date: 2017-02-02 Impact factor: 3.164

Enantioselective synthesis of (+)-cephalostatin 1.

1. Chemical synthesis of 7-oxygenated 12α-hydroxy steroid derivatives to enable the biochemical characterization of cytochrome P450 8B1, the oxysterol 12α-hydroxylase enzyme implicated in cardiovascular health and obesity.

2. Natural products reveal cancer cell dependence on oxysterol-binding proteins.

3. Synthesis and evaluation of a fluorescent ritterazine-cephalostatin hybrid.

4. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

5. Ritterostatin G_N 1_N , a Cephalostatin-Ritterazine Bis-steroidal Pyrazine Hybrid, Selectively Targets GRP78.

6. Scalable C-H Oxidation with Copper: Synthesis of Polyoxypregnanes.

7. The cephalostatins. 22. synthesis of bis-steroidal pyrazine pyrones (1).

8. Decoding the Mechanism of Intramolecular Cu-Directed Hydroxylation of sp³ C-H Bonds.

9. Asymmetric synthesis of dihydroindanes by convergent alkoxide-directed metallacycle-mediated bond formation.

10. A convergent total synthesis of the potent cephalostatin/ritterazine hybrid -25-epi ritterostatin GN1N.