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Literature DB >> 16756299

Unified total synthesis of pteriatoxins and their diastereomers.

Fumiyoshi Matsuura¹, René Peters, Masahiro Anada, Scott S Harried, Junliang Hao, Yoshito Kishi.

Abstract

A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 16756299 PMCID： PMC2515931 DOI： 10.1021/ja0618954

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

5 in total

1. A stereoselective synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A.

Authors: S Nakamura; J Inagaki; T Sugimoto; M Kudo; M Nakajima; S Hashimoto
Journal: Org Lett Date: 2001-12-13 Impact factor: 6.005

2. Carbonminus signCarbon Bond Formations Involving Organochromium(III) Reagents.

Authors: Alois Fürstner
Journal: Chem Rev Date: 1999-04-14 Impact factor: 60.622

3. A formal total synthesis of (+)-pinnatoxin A.

Authors: Satoshi Sakamoto; Hayato Sakazaki; Koji Hagiwara; Kei Kamada; Kento Ishii; Takeshi Noda; Masayuki Inoue; Masahiro Hirama
Journal: Angew Chem Int Ed Engl Date: 2004-12-03 Impact factor: 15.336

4. An approach to the imine ring system of pinnatoxins.

Authors: Matthew J Pelc; Armen Zakarian
Journal: Org Lett Date: 2005-04-14 Impact factor: 6.005

5. Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water.

Authors: Ren-Hua Fan; Xue-Long Hou
Journal: J Org Chem Date: 2003-02-07 Impact factor: 4.354

5 in total

13 in total

1. Stereochemistry of pteriatoxins A, B, and C.

Authors: Junliang Hao; Fumiyoshi Matsuura; Yoshito Kishi; Masaki Kita; Daisuke Uemura; Naoki Asai; Takashi Iwashita
Journal: J Am Chem Soc Date: 2006-06-21 Impact factor: 15.419

2. INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors: Tadeusz F Molinski; Brandon I Morinaka
Journal: Tetrahedron Date: 2012-11-18 Impact factor: 2.457

3. Total synthesis and stereochemistry of pinnatoxins B and C.

Authors: Fumiyoshi Matsuura; Junliang Hao; Reinhard Reents; Yoshito Kishi
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

4. Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.

Authors: Romulo Araoz; Denis Servent; Jordi Molgó; Bogdan I Iorga; Carole Fruchart-Gaillard; Evelyne Benoit; Zhenhua Gu; Craig Stivala; Armen Zakarian
Journal: J Am Chem Soc Date: 2011-06-17 Impact factor: 15.419

Review 5. Cyclic imine toxins from dinoflagellates: a growing family of potent antagonists of the nicotinic acetylcholine receptors.

Authors: Jordi Molgó; Pascale Marchot; Rómulo Aráoz; Evelyne Benoit; Bogdan I Iorga; Armen Zakarian; Palmer Taylor; Yves Bourne; Denis Servent
Journal: J Neurochem Date: 2017-03-21 Impact factor: 5.372

Unified total synthesis of pteriatoxins and their diastereomers.

1. A stereoselective synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A.

2. Carbonminus signCarbon Bond Formations Involving Organochromium(III) Reagents.

3. A formal total synthesis of (+)-pinnatoxin A.

4. An approach to the imine ring system of pinnatoxins.

5. Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water.

1. Stereochemistry of pteriatoxins A, B, and C.

2. INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

3. Total synthesis and stereochemistry of pinnatoxins B and C.

4. Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.

Review 5. Cyclic imine toxins from dinoflagellates: a growing family of potent antagonists of the nicotinic acetylcholine receptors.

6. Marine Toxins with Spiroimine Rings: Total Synthesis of Pinnatoxin A.

7. Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer.

8. Thiol Probes To Detect Electrophilic Natural Products Based on Their Mechanism of Action.

9. Enantioselective total synthesis of the marine toxin (-)-gymnodimine employing a Barbier-type macrocyclization.

10. Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment.