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Literature DB >> 20351791

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

Ling-Feng You¹, Richard P Hsung, Aaron A Bedermann, Aleksey V Kurdyumov, Yu Tang, Grant S Buchanan, Kevin P Cole.

Abstract

An enantioselective synthesis of the ABD-ring of (-)-phomactin A is described here. The sequence features Rawal's asymmetric Diels-Alder cycloaddition. The overall length is significantly reduced from our previous attempt.

Entities: CellLine Chemical Species

Year: 2008 PMID： 20351791 PMCID： PMC2846367

Source DB: PubMed Journal: Adv Synth Catal ISSN： 1615-4150 Impact factor: 5.837

31 in total

1. Design and development of highly effective Lewis acid catalysts for enantioselective Diels-Alder reactions.

Authors: Yong Huang; Tetsuo Iwama; Viresh H Rawal
Journal: J Am Chem Soc Date: 2002-05-29 Impact factor: 15.419

2. Application of chiral cationic catalysts to several classical syntheses of racemic natural products transforms them into highly enantioselective pathways.

Authors: Qi-Ying Hu; Gang Zhou; E J Corey
Journal: J Am Chem Soc Date: 2004-10-27 Impact factor: 15.419

3. Facile synthesis of 1,3,7-trihydroxyxanthone and its regioselective coupling reactions with prenal: simple and efficient access to osajaxanthone and nigrolineaxanthone F.

Authors: Mukulesh Mondal; Vedavati G Puranik; Narshinha P Argade
Journal: J Org Chem Date: 2006-06-23 Impact factor: 4.354

4. An unusual cationic [2 + 2] cycloaddition in a divergent total synthesis of hongoquercin A and rhododaurichromanic acid A.

Authors: Aleksey V Kurdyumov; Richard P Hsung
Journal: J Am Chem Soc Date: 2006-05-17 Impact factor: 15.419

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

6. Use of thallium(I) ethoxide in Suzuki cross coupling reactions.

Authors: S A Frank; H Chen; R K Kunz; M J Schnaderbeck; W R Roush
Journal: Org Lett Date: 2000-08-24 Impact factor: 6.005

7. 1-Amino-3-siloxy-1,3-butadienes: Highly Reactive Dienes for the Diels-Alder Reaction.

Authors: Sergey A. Kozmin; Jacob M. Janey; Viresh H. Rawal
Journal: J Org Chem Date: 1999-04-30 Impact factor: 4.354

8. An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.

Authors: Sergey A Kozmin; Tetsuo Iwama; Yong Huang; Viresh H Rawal
Journal: J Am Chem Soc Date: 2002-05-01 Impact factor: 15.419

9. A modular and concise total synthesis of (+/-)-daurichromenic acid and analogues.

Authors: Hongjuan Hu; Tyler J Harrison; Peter D Wilson
Journal: J Org Chem Date: 2004-05-28 Impact factor: 4.354

10. Intramolecular cyclohexadienone annulations of Fischer carbene complexes: model studies for the synthesis of Phomactins.

Authors: Jie Huang; Huan Wang; Chunrui Wu; William D Wulff
Journal: Org Lett Date: 2007-06-20 Impact factor: 6.005

7 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

2. Total synthesis of phomactin A.

Authors: Yu Tang; Kevin P Cole; Grant S Buchanan; Gang Li; Richard P Hsung
Journal: Org Lett Date: 2009-04-02 Impact factor: 6.005

3. Cascade cyclizations of acyclic and macrocyclic alkynones: studies toward the synthesis of phomactin A.

Authors: Jennifer Ciesielski; Vincent Gandon; Alison J Frontier
Journal: J Org Chem Date: 2013-06-10 Impact factor: 4.354

4. Constructing the Architecturally Distinctive ABD-Tricycle of Phomactin A through an Intramolecular Oxa-[3 + 3] Annulation Strategy.

Authors: Grant S Buchanan; Kevin P Cole; Gang Li; Yu Tang; Ling-Feng You; Richard P Hsung
Journal: Tetrahedron Date: 2011-12-30 Impact factor: 2.457