Literature DB >> 24273477

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:  

Keywords:  Cr(III)-salen catalyst; Rawal’s 1-amino-3-siloxy-1,3-butadiene; asymmetric Diels-Alder cycloaddition; intramolecular oxa-[3 + 3] annulation; phomactin A

Year:  2008        PMID： 24273477      PMCID： PMC3834967          DOI： 10.1002/adsc.200800552

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


  49 in total

1.  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

2.  A Sakurai-Prins-Ritter sequence for the three-component diastereoselective synthesis of 4-amino tetrahydropyrans.

Authors:  Oleg L Epstein; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

3.  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

4.  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

5.  Studies toward the tricyclic core of phomactin A. Synthesis of the reduced furanochroman subunit.

Authors:  P P Seth; N I Totah
Journal:  Org Lett       Date:  2000-08-10       Impact factor: 6.005

6.  Broadly effective enantioselective Diels-Alder reactions of 1-amino-substituted-1,3-butadienes.

Authors:  Yong Huang; Tetsuo Iwama; Viresh H Rawal
Journal:  Org Lett       Date:  2002-04-04       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.  A total synthesis of phomactin A.

Authors:  William P D Goldring; Gerald Pattenden
Journal:  Chem Commun (Camb)       Date:  2002-08-21       Impact factor: 6.222
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