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Literature DB >> 17020327

Total synthesis of (+/-)-clavubicyclone.

Hisanaka Ito¹, Shunta Takeguchi, Takahiro Kawagishi, Kazuo Iguchi.

Abstract

[reaction: see text] The total synthesis of racemic clavubicyclone (1), which was isolated from Okinawan soft coral by our group, is described. The bicyclo[3.2.1]octane skeleton was prepared by Cope rearrangement of a divinylcyclopropane derivative. Three functional groups on the skeleton were constructed by Barton decarboxylation, Wittig reaction, and alkylation.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 17020327 DOI： 10.1021/ol061947u

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

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Cited

7 in total

1. Cobalt(II)-catalyzed asymmetric olefin cyclopropanation with α-ketodiazoacetates.

Authors: Xue Xu; Shifa Zhu; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal: Angew Chem Int Ed Engl Date: 2013-09-20 Impact factor: 15.336

2. Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors: Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal: J Am Chem Soc Date: 2015-08-28 Impact factor: 15.419

7. A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes.

Authors: Eduardo de Pedro Beato; Davide Spinnato; Wei Zhou; Paolo Melchiorre
Journal: J Am Chem Soc Date: 2021-07-28 Impact factor: 15.419

7 in total

Total synthesis of (+/-)-clavubicyclone.

1. Cobalt(II)-catalyzed asymmetric olefin cyclopropanation with α-ketodiazoacetates.

2. Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Review 3. Recent applications of the divinylcyclopropane-cycloheptadiene rearrangement in organic synthesis.

4. Enantioselective, Convergent Synthesis of the Ineleganolide Core by a Tandem Annulation Cascade.

5. Assembly of Complex 1,4-Cycloheptadienes by (4+3) Cycloaddition of Rhodium(II) and Gold(I) Non-Acceptor Carbenes.

6. 1,2-Carboboration of Arylallenes by In Situ Generated Alkenylboranes for the Synthesis of 1,4-Dienes.

7. A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes.