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 Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization.

Literature DB >> 12580592

Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization.

Abstract

A total synthesis of (+)-phomactin A is described using a B-alkyl Suzuki macrocyclization to incorporate the isolated trisubstituted olefin. This macrocyclization was accomplished with the sensitive hydrated furan ring in place. (R)-(+)-pulegone was used to establish the highly substituted cyclohexene core of the molecule.

Entities: Chemical

Mesh：

Substances：

Year: 2003 PMID： 12580592 DOI： 10.1021/ja0296531

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

Keyword Cloud
Cited

23 in total

1. Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.

Authors: Grant S Buchanan; Kevin P Cole; Yu Tang; Richard P Hsung
Journal: J Org Chem Date: 2011-08-05 Impact factor: 4.354

Review 2. Transition Metal-Mediated C-C Single Bond Cleavage: Making the Cut in Total Synthesis.

Authors: Brian Wang; Melecio A Perea; Richmond Sarpong
Journal: Angew Chem Int Ed Engl Date: 2020-08-24 Impact factor: 15.336

3. An Enantioselective Synthesis of the ABD Tricycle for (-)-Phomactin A Featuring Rawal's Asymmetric Diels-Alder Cycloaddition.

Authors: Ling-Feng You; Richard P Hsung; Aaron A Bedermann; Aleksey V Kurdyumov; Yu Tang; Grant S Buchanan; Kevin P Cole
Journal: Adv Synth Catal Date: 2008-12-18 Impact factor: 5.837

4. Studies toward the synthesis of phomactin A. An approach to the macrocyclic core.

Authors: Dawei Teng; Bo Wang; Alex J Augatis; Nancy I Totah
Journal: Tetrahedron Lett Date: 2007-06-25 Impact factor: 2.415

5. Total synthesis of (+/-)-phomactin B2 via an intramolecular cyclohexadienone annulation of a chromium carbene complex.

Authors: Jie Huang; Chunrui Wu; William D Wulff
Journal: J Am Chem Soc Date: 2007-10-12 Impact factor: 15.419

Review 6. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors: Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal: Chem Rev Date: 2011-02-14 Impact factor: 60.622

Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization.

1. Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.

Review 2. Transition Metal-Mediated C-C Single Bond Cleavage: Making the Cut in Total Synthesis.

3. An Enantioselective Synthesis of the ABD Tricycle for (-)-Phomactin A Featuring Rawal's Asymmetric Diels-Alder Cycloaddition.

4. Studies toward the synthesis of phomactin A. An approach to the macrocyclic core.

5. Total synthesis of (+/-)-phomactin B2 via an intramolecular cyclohexadienone annulation of a chromium carbene complex.

Review 6. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Review 7. Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

8. Synthesis and evaluation of novel analogues of ripostatins.

9. Total synthesis and stereochemical assignment of (-)-ushikulide A.

10. Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides.