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Literature DB >> 16928078

Improved synthesis of the ABCDE fragment of brevetoxin A.

Michael T Crimmins¹, Patrick J McDougall, J Michael Ellis.

Abstract

A second-generation synthesis of the BCDE fragment of brevetoxin A is described. Novel reactions were developed that extend the utility of the asymmetric glycolate alkylation reaction and improve scale-up to provide gram quantities of the B and E subunits. Significant improvements to the convergent assembly of the tetracycle were also realized. In addition, formation of the A ring lactone was accomplished to complete the ABCDE pentacycle.

Entities: Chemical

Mesh：

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Year: 2006 PMID： 16928078 DOI： 10.1021/ol0615782

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

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Cited

6 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

Improved synthesis of the ABCDE fragment of brevetoxin A.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Synthesis of the QRSTU domain of maitotoxin and its 85-epi- and 86-epi-diastereoisomers.

3. Total synthesis and stereochemical assignment of (-)-ushikulide A.

4. Total synthesis of brevetoxin A.

5. Enantioselective total synthesis of brevetoxin A: convergent coupling strategy and completion.

6. Studies for the synthesis of xenicane diterpenes. A stereocontrolled total synthesis of 4-hydroxydictyolactone.