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Literature DB >> 18254629

Total synthesis of +-superstolide A.

Mariola Tortosa¹, Neal A Yakelis, William R Roush.

Abstract

A convergent and highly stereocontrolled synthesis of +-superstolide A (1) has been accomplished. Key steps of this synthesis include the intramolecular Suzuki reaction of 26 and the highly diastereoselective transannular Diels-Alder cyclization of macrocyclic octaene 3.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 18254629 DOI： 10.1021/ja710238h

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

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Cited

10 in total

1. Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities.

Authors: Alpay Dermenci; Philipp S Selig; Robert A Domaoal; Krasimir A Spasov; Karen S Anderson; Scott J Miller
Journal: Chem Sci Date: 2011-08-01 Impact factor: 9.825

2. Controlling the facial selectivity of asymmetric [4+2] cyclo-additions: a concise synthesis of the cis-decalin core structure of superstolides A and B.

Authors: Lei Chen; Zhengmao Hua; Gangqin Li; Zhendong Jin
Journal: Org Lett Date: 2011-06-14 Impact factor: 6.005

3. Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes.

Authors: Holly A Reichard; Martin McLaughlin; Ming Z Chen; Glenn C Micalizio
Journal: European J Org Chem Date: 2010-01

4. Development of a general, sequential, ring-closing metathesis/intramolecular cross-coupling reaction for the synthesis of polyunsaturated macrolactones.

Authors: Scott E Denmark; Joseck M Muhuhi
Journal: J Am Chem Soc Date: 2010-08-25 Impact factor: 15.419

Total synthesis of +-superstolide A.

1. Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities.

2. Controlling the facial selectivity of asymmetric [4+2] cyclo-additions: a concise synthesis of the cis-decalin core structure of superstolides A and B.

3. Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes.

4. Development of a general, sequential, ring-closing metathesis/intramolecular cross-coupling reaction for the synthesis of polyunsaturated macrolactones.

5. Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

6. Total synthesis of (+)-superstolide A.

Review 7. Chikungunya: a potentially emerging epidemic?

8. A Convenient Reagent for Aldehyde to Alkyne Homologation.

9. Design, synthesis, and biological evaluation of truncated superstolide A.

10. Enantioselective synthesis of (-)-maoecrystal V by enantiodetermining C-H functionalization.