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Literature DB >> 17480091

A formal total synthesis of (+)-zincophorin. Observation of an unusual urea-directed Stork-Crabtree hydrogenation.

Abstract

A formal total synthesis of (+)-zincophorin via interception of Miyashita's advanced intermediates is described here. This effort features the first synthetic application of an inverse demand hetero [4 + 2] cycloaddition of a chiral allenamide, and the observation of an unusual urea directed Stork-Crabtree hydrogenation.

Entities: Chemical

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Year: 2007 PMID： 17480091 DOI： 10.1021/ol070791a

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

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Cited

8 in total

1. Evolution of an Efficient and Scalable Nine-Step (Longest Linear Sequence) Synthesis of Zincophorin Methyl Ester.

Authors: Liang-An Chen; Melissa A Ashley; James L Leighton
Journal: J Am Chem Soc Date: 2017-03-15 Impact factor: 15.419

2. Studies on a urea-directed Stork-Crabtree hydrogenation. Synthesis of the C1-C9 subunit of (+)-zincophorin.

Authors: Zhenlei Song; Richard P Hsung; Ting Lu; Andrew G Lohse
Journal: J Org Chem Date: 2007-11-03 Impact factor: 4.354

3. Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl Ester.

Authors: Zachary A Kasun; Xin Gao; Radoslaw M Lipinski; Michael J Krische
Journal: J Am Chem Soc Date: 2015-07-13 Impact factor: 15.419

A formal total synthesis of (+)-zincophorin. Observation of an unusual urea-directed Stork-Crabtree hydrogenation.

1. Evolution of an Efficient and Scalable Nine-Step (Longest Linear Sequence) Synthesis of Zincophorin Methyl Ester.

2. Studies on a urea-directed Stork-Crabtree hydrogenation. Synthesis of the C1-C9 subunit of (+)-zincophorin.

3. Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl Ester.

4. Toward more "ideal" polyketide natural product synthesis: a step-economical synthesis of zincophorin methyl ester.

5. Saucy-Marbet Rearrangements of Alkynyl Halides in the Synthesis of Highly Enantiomerically Enriched Allenyl Halides.

Review 6. Challenges in the synthesis of a unique mono-carboxylic acid antibiotic, (+)-zincophorin.

7. Synthesis of amido-spiro[2.2]pentanes via Simmons-Smith cyclopropanation of allenamides.

Review 8. Allenamides: a powerful and versatile building block in organic synthesis.