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Literature DB >> 21503271

Stereoselective Synthesis of the Decahydrofluorene Core of the Hirsutellones.

Abstract

A stereoselective synthesis of the decahydrofluorene core of the hirsutellones was accomplished in 8 steps and in 43% overall yield. The key step of the synthesis is the highly stereoselective intramolecular Diels-Alder cyclization of the siloxacyclopentene constrained tetraene 1.

Entities: Chemical Disease Mutation Species

Year: 2011 PMID： 21503271 PMCID： PMC3077760 DOI： 10.1016/j.tetlet.2010.10.111

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

10 in total

Review 1. Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Authors: Ken-Ichi Takao; Ryosuke Munakata; Kin-ichi Tadano
Journal: Chem Rev Date: 2005-12 Impact factor: 60.622

Review 2. Recent applications of intramolecular Diels-Alder reactions to natural product synthesis.

Authors: Martin Juhl; David Tanner
Journal: Chem Soc Rev Date: 2009-07-29 Impact factor: 54.564

3. Catalytic enantioselective Diels-Alder reaction by self-assembly of the components on a Lewis acid template.

Authors: Dale E Ward; Michael Santos Souweha
Journal: Org Lett Date: 2005-08-04 Impact factor: 6.005

4. Hirsutellone F, a dimer of antitubercular alkaloids from the seed fungus Trichoderma species BCC 7579.

Authors: Masahiko Isaka; Wai Prathumpai; Patcharaporn Wongsa; Morakot Tanticharoen
Journal: Org Lett Date: 2006-06-22 Impact factor: 6.005

5. Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride.

Authors: Cheryl L Heitzman; William T Lambert; Eric Mertz; J Brad Shotwell; Jennifer M Tinsley; Porino Va; William R Roush
Journal: Org Lett Date: 2005-06-09 Impact factor: 6.005

6. Stereochemistry of the allylation and crotylation reactions of alpha-methyl-beta-hydroxy aldehydes with allyl- and crotyltrifluorosilanes. Synthesis of anti,anti-dipropionate stereotriads and stereodivergent pathways for the reactions with 2,3-anti- and 2,3-syn-alpha-methyl-beta-hydroxy aldehydes.

Authors: Sherry R Chemler; William R Roush
Journal: J Org Chem Date: 2003-02-21 Impact factor: 4.354

7. Unusual Tandem alkynylation and trans-hydrosilylation to form oxasilacyclopentenes.

Authors: Sarah V Maifeld; Daesung Lee
Journal: Org Lett Date: 2005-10-27 Impact factor: 6.005

8. Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes.

Authors: Geoff T Halvorsen; William R Roush
Journal: Org Lett Date: 2007-05-05 Impact factor: 6.005

9. Total synthesis of hirsutellone B.

Authors: K C Nicolaou; David Sarlah; T Robert Wu; Weiqiang Zhan
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

10. A rapid, asymmetric synthesis of the decahydrofluorene core of the hirsutellones.

Authors: S David Tilley; Keith P Reber; Erik J Sorensen
Journal: Org Lett Date: 2009-02-05 Impact factor: 6.005

10 in total

5 in total

Stereoselective Synthesis of the Decahydrofluorene Core of the Hirsutellones.

Review 1. Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Review 2. Recent applications of intramolecular Diels-Alder reactions to natural product synthesis.

3. Catalytic enantioselective Diels-Alder reaction by self-assembly of the components on a Lewis acid template.

4. Hirsutellone F, a dimer of antitubercular alkaloids from the seed fungus Trichoderma species BCC 7579.

5. Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride.

7. Unusual Tandem alkynylation and trans-hydrosilylation to form oxasilacyclopentenes.

8. Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes.

9. Total synthesis of hirsutellone B.

10. A rapid, asymmetric synthesis of the decahydrofluorene core of the hirsutellones.

1. Bioinspired synthesis of hirsutellones A, B, and C.

Review 2. A brief history of antibiotics and select advances in their synthesis.

3. Toward a synthesis of hirsutellone B by the concept of double cyclization.

4. Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

Review 5. Macrocyclic drugs and synthetic methodologies toward macrocycles.