Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

Literature DB >> 20527780

A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

Mahesh P Paudyal¹, Nigam P Rath, Christopher D Spilling.

Abstract

Homoallylation of aldehydes with isoprene and triethylborane catalyzed by Ni(acac)(2) gave hydroxyalkenes in good yield with excellent regio- and stereoselectivity. Cross metathesis of the hydroxyalkenes with methyl acrylate using second-generation Grubbs catalyst and copper(I) iodide afforded alpha,beta-unsaturated esters, which underwent cyclization in the presence of DBU to produce tetrahydrofurans with the correct relative configuration for the C1-C9 fragment of amphidinolides C, C2, and F.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2010 PMID： 20527780 PMCID： PMC2896498 DOI： 10.1021/ol100959a

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

17 in total

1. Nickel-Catalyzed Homoallylation of Aldehydes in the Presence of Water and Alcohols We thank Mr. Y. Ohhama, NMR Facility, for his outstanding technical assistance. Financial support from the Ministry of Education, Science, Sports, and Culture, Japanese Government, Grant-in-Aid for Scientific Research B, is acknowledged.

Authors: Masanari Kimura; Akihiro Ezoe; Shuji Tanaka; Yoshinao Tamaru
Journal: Angew Chem Int Ed Engl Date: 2001-10-01 Impact factor: 15.336

2. Absolute stereochemistry of amphidinolide C.

Authors: T Kubota; M Tsuda; J Kobayashi
Journal: Org Lett Date: 2001-05-03 Impact factor: 6.005

3. Amphidinolides T2, T3, and T4, new 19-membered macrolides from the dinoflagellate Amphidinium sp. and the biosynthesis of amphidinolide T1.

Authors: J Kobayashi; T Kubota; T Endo; M Tsuda
Journal: J Org Chem Date: 2001-01-12 Impact factor: 4.354

4. Amphidinolide T, novel 19-membered macrolide from marine dinoflagellate Amphidinium sp.

Authors: M Tsuda; T Endo; J Kobayashi
Journal: J Org Chem Date: 2000-03-10 Impact factor: 4.354

5. A general model for selectivity in olefin cross metathesis.

Authors: Arnab K Chatterjee; Tae-Lim Choi; Daniel P Sanders; Robert H Grubbs
Journal: J Am Chem Soc Date: 2003-09-17 Impact factor: 15.419

6. Synthesis of nonracemic allylic hydroxy phosphonates via alkene cross metathesis.

Authors: Anyu He; Bingli Yan; Anchalee Thanavaro; Christopher D Spilling; Nigam P Rath
Journal: J Org Chem Date: 2004-12-10 Impact factor: 4.354

7. Synthesis of the C11-C29 fragment of amphidinolide F.

Authors: J Brad Shotwell; William R Roush
Journal: Org Lett Date: 2004-10-14 Impact factor: 6.005

8. Catalytic generation of activated carboxylates: direct, stereoselective synthesis of beta-hydroxyesters from epoxyaldehydes.

Authors: Kenneth Yu-Kin Chow; Jeffrey W Bode
Journal: J Am Chem Soc Date: 2004-07-07 Impact factor: 15.419

9. Amphidinolide Y, a novel 17-membered macrolide from dinoflagellate Amphidinium sp.: plausible biogenetic precursor of amphidinolide X.

Authors: Masashi Tsuda; Naoko Izui; Kazutaka Shimbo; Masaaki Sato; Eri Fukushi; Jun Kawabata; Jun'ichi Kobayashi
Journal: J Org Chem Date: 2003-11-14 Impact factor: 4.354

A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

2. Absolute stereochemistry of amphidinolide C.

3. Amphidinolides T2, T3, and T4, new 19-membered macrolides from the dinoflagellate Amphidinium sp. and the biosynthesis of amphidinolide T1.

4. Amphidinolide T, novel 19-membered macrolide from marine dinoflagellate Amphidinium sp.

5. A general model for selectivity in olefin cross metathesis.

6. Synthesis of nonracemic allylic hydroxy phosphonates via alkene cross metathesis.

7. Synthesis of the C11-C29 fragment of amphidinolide F.

8. Catalytic generation of activated carboxylates: direct, stereoselective synthesis of beta-hydroxyesters from epoxyaldehydes.

9. Amphidinolide Y, a novel 17-membered macrolide from dinoflagellate Amphidinium sp.: plausible biogenetic precursor of amphidinolide X.

Review 10. Amphidinolides, bioactive macrolides from symbiotic marine dinoflagellates.

1. Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)-C(15) Segment.

2. Enantioselective total synthesis of amphidinolide F.

3. Convergent Synthesis of the C1-C29 Framework of Amphidinolide F.

4. Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F.

5. Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F.

6. Chagosensine: A Riddle Wrapped in a Mystery Inside an Enigma.