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Literature DB >> 11405752

Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes.

Abstract

[see reaction]. A synthesis of tetracycle 2 corresponding to the C(11)-C(26) fragment of pectenotoxin II is described. The synthesis features two highly stereoselective [3 + 2]-annulation reactions of chiral allylsilanes, generated via allylboration of aldehydes with the chiral gamma-silylallylborane 4 or the gamma-silylallylboronate 19, for construction of the highly substituted C and E rings.

Entities: Chemical

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Year: 2001 PMID： 11405752 DOI： 10.1021/ol0160250

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

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Cited

14 in total

1. Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

Authors: Jennifer M Tinsley; Eric Mertz; Pek Y Chong; Robert-André F Rarig; William R Roush
Journal: Org Lett Date: 2005-09-15 Impact factor: 6.005

2. Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

Authors: John P Wolfe; Michael B Hay
Journal: Tetrahedron Date: 2007-01-08 Impact factor: 2.457

3. Iridium-catalyzed anti-diastereo- and enantioselective carbonyl (trimethylsilyl)allylation from the alcohol or aldehyde oxidation level.

Authors: Soo Bong Han; Xin Gao; Michael J Krische
Journal: J Am Chem Soc Date: 2010-07-07 Impact factor: 15.419

Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes.

1. Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

2. Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

3. Iridium-catalyzed anti-diastereo- and enantioselective carbonyl (trimethylsilyl)allylation from the alcohol or aldehyde oxidation level.

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

5. Surveying approaches to the formation of carbon-carbon bonds between a pyran and an adjacent ring.

6. Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C.

7. Diastereoselective synthesis of the pectenotoxin 2 non-anomeric AB spiroacetal.

8. Studies for the total synthesis of amphidinolide P.

9. Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

10. Synthesis of the C1-C26 hexacyclic subunit of pectenotoxin 2.