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Literature DB >> 12599485

Synthetic and mechanistic studies of the retro-Claisen rearrangement. 4. An application to the total synthesis of (+)-Laurenyne.

Robert K Boeckman¹, Jing Zhang, Michael R Reeder.

Abstract

[formula: see text] A novel asymmetric total synthesis of marine natural product (+)-Laurenyne has been achieved. The key elements of the strategy are the sequential metal ion-templated SN2' cyclization affording a highly functionalized chiral vinyl cyclobutane and a retro-Claisen rearrangement for the construction of an eight-membered ring ether.

Entities: Chemical Gene

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Year: 2002 PMID： 12599485 DOI： 10.1021/ol0267174

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

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Cited

5 in total

1. Mo-catalyzed asymmetric olefin metathesis in target-oriented synthesis: enantioselective synthesis of (+)-africanol.

Authors: Gabriel S Weatherhead; G A Cortez; Richard R Schrock; Amir H Hoveyda
Journal: Proc Natl Acad Sci U S A Date: 2004-03-31 Impact factor: 11.205

2. Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.

Authors: Pilho Kim; Yong-Mei Zhang; Gautham Shenoy; Quynh-Anh Nguyen; Helena I Boshoff; Ujjini H Manjunatha; Michael B Goodwin; John Lonsdale; Allen C Price; Darcie J Miller; Ken Duncan; Stephen W White; Charles O Rock; Clifton E Barry; Cynthia S Dowd
Journal: J Med Chem Date: 2006-01-12 Impact factor: 7.446

Synthetic and mechanistic studies of the retro-Claisen rearrangement. 4. An application to the total synthesis of (+)-Laurenyne.

1. Mo-catalyzed asymmetric olefin metathesis in target-oriented synthesis: enantioselective synthesis of (+)-africanol.

2. Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.

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

4. Chemical Composition of Laurencia obtusa Extract and Isolation of a New C₁₅-Acetogenin.

5. Unorthodox synthesis, biological activity and DFT studies of novel and multifunctionalized naphthoxocine derivatives.

Synthetic and mechanistic studies of the retro-Claisen rearrangement. 4. An application to the total synthesis of (+)-Laurenyne.

1. Mo-catalyzed asymmetric olefin metathesis in target-oriented synthesis: enantioselective synthesis of (+)-africanol.

2. Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.

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

4. Chemical Composition of Laurencia obtusa Extract and Isolation of a New C15-Acetogenin.

5. Unorthodox synthesis, biological activity and DFT studies of novel and multifunctionalized naphthoxocine derivatives.

4. Chemical Composition of Laurencia obtusa Extract and Isolation of a New C₁₅-Acetogenin.