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Literature DB >> 16321034

Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine.

Abstract

[chemical reaction: see text]. Concise formal syntheses of marine alkaloids (+/-)-pinnaic acid (1) and (+/-)-halichlorine (2) have been accomplished from a common intermediate. The syntheses illustrate the utility of selective olefin cross metathesis methodologies for the elaboration of advanced synthetic intermediates in complex molecule synthesis.

Entities: Chemical

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Year: 2005 PMID： 16321034 PMCID： PMC2536714 DOI： 10.1021/ol0525009

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

26 in total

1. Total Synthesis and Proof of Stereochemistry of Natural and Unnatural Pinnaic Acids: A Remarkable Long-Range Stereochemical Effect in the Reduction of 17-Oxo Precursors of the Pinnaic Acids This work was supported by the National Institutes of Health (Grant Numbers: CA28824). Postdoctoral Fellowship support is gratefully acknowledged by M.W.C. (U.S. Army BCRP, DAMD17-98-1-8154). We thank Dr. George Sukenick of the MSKCC NMR Core Facility for NMR and mass spectral analyses. We would like to thank professor Nakanishi for his supportive interest in the project.

Authors: Matthew W. Carson; Guncheol Kim; Samuel J. Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2001-12-03 Impact factor: 15.336

2. Recent advances in the Baylis-Hillman reaction and applications.

Authors: Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
Journal: Chem Rev Date: 2003-03 Impact factor: 60.622

3. New stereoselective entry to azaspirocyclic nucleus of halichlorine and pinnaic acids by radical translocation/cyclization reaction.

Authors: Kiyosei Takasu; Hiroshi Ohsato; Masataka Ihara
Journal: Org Lett Date: 2003-08-21 Impact factor: 6.005

4. Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.

Authors: David G Washburn; Richard W Heidebrecht; Stephen F Martin
Journal: Org Lett Date: 2003-09-18 Impact factor: 6.005

5. Stereoselective total synthesis of dihydrocorynantheol.

Authors: Alexander Deiters; Stephen F Martin
Journal: Org Lett Date: 2002-09-19 Impact factor: 6.005

6. Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol.

Authors: Timothy W Funk; Jon Efskind; Robert H Grubbs
Journal: Org Lett Date: 2005-01-20 Impact factor: 6.005

7. Angiogenesis mediated by soluble forms of E-selectin and vascular cell adhesion molecule-1.

Authors: A E Koch; M M Halloran; C J Haskell; M R Shah; P J Polverini
Journal: Nature Date: 1995-08-10 Impact factor: 49.962

8. Efficient synthesis of the azaspirocyclic core structure of halichlorine and pinnaic acid by intramolecular acylnitroso ene reaction.

Authors: Yosuke Matsumura; Sakae Aoyagi; Chihiro Kibayashi
Journal: Org Lett Date: 2003-09-04 Impact factor: 6.005

9. Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.

Authors: Christopher E Neipp; Stephen F Martin
Journal: J Org Chem Date: 2003-11-14 Impact factor: 4.354

10. A formal total synthesis of (+/-)-halichlorine and (+/-)-pinnaic acid.

Authors: Yosuke Matsumura; Sakae Aoyagi; Chihiro Kibayashi
Journal: Org Lett Date: 2004-03-18 Impact factor: 6.005

12 in total

1. Iminium Ion Cascade Reactions: Stereoselective Synthesis of Quinolizidines and Indolizidines.

Authors: Shawn M Amorde; Ivan T Jewett; Stephen F Martin
Journal: Tetrahedron Date: 2009-04-19 Impact factor: 2.457

2. Concise, enantioselective total synthesis of (-)-alstonerine.

Authors: Kenneth A Miller; Stephen F Martin
Journal: Org Lett Date: 2007-02-14 Impact factor: 6.005

3. Novel approach to the lundurine alkaloids: synthesis of the tetracyclic core.

Authors: Suvi T M Orr; Jianhua Tian; Meike Niggemann; Stephen F Martin
Journal: Org Lett Date: 2011-09-02 Impact factor: 6.005

4. Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors: Stephen F Martin
Journal: J Org Chem Date: 2017-09-15 Impact factor: 4.354

5. Facile Syntheses of Substituted, Conformationally-Constrained Benzoxazocines and Benzazocines via Sequential Multicomponent Assembly and Cyclization.

Authors: James J Sahn; Stephen F Martin
Journal: Tetrahedron Lett Date: 2011-12-21 Impact factor: 2.415

6. Concise total synthesis of (+/-)-pseudotabersonine via double ring-closing metathesis strategy.

Authors: Bo Cheng; James D Sunderhaus; Stephen F Martin
Journal: Org Lett Date: 2010-08-20 Impact factor: 6.005

7. Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis.

Authors: Jason A Deck; Stephen F Martin
Journal: Org Lett Date: 2010-06-04 Impact factor: 6.005

8. Diastereoselective synthesis of cyclopentapyridazinones via radical cyclization: synthetic studies toward halichlorine.

Authors: Gary E Keck; Stacey A Heumann
Journal: Org Lett Date: 2008-09-25 Impact factor: 6.005

9. Applications of Ring Closing Metathesis. Total Synthesis of (±)-Pseudotabersonine.

Authors: Bo Cheng; James D Sunderhaus; Stephen F Martin
Journal: Tetrahedron Date: 2015-09-30 Impact factor: 2.457

10. Toward the total synthesis of FR901483: concise synthesis of the azatricyclic skeleton.

Authors: Suvi T M Simila; Stephen F Martin
Journal: J Org Chem Date: 2007-06-08 Impact factor: 4.354