ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
Recently Viewed
You have not visited any articles yet, Please visit some articles to see contents here.
CONTENT TYPES

Total Synthesis of Phorboxazole A. 1. Preparation of Four Subunits

View Author Information
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331
Cite this: Org. Lett. 2006, 8, 26, 6039–6042
Publication Date (Web):November 22, 2006
https://doi.org/10.1021/ol062530r
Copyright © 2006 American Chemical Society
Article Views
1754
Altmetric
-
Citations
LEARN ABOUT THESE METRICS
Read OnlinePDF (104 KB)
Supporting Info (1)»

Abstract

Abstract Image

Four subunits of the potent antitumor agent phorboxazole A were constructed; fragments C20−C32 and C9−C19 containing tetrahydropyrans A and B, respectively, were assembled using palladium-catalyzed intramolecular alkoxycarbonylation.

*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Supporting Information Available

ARTICLE SECTIONS
Jump To

Detailed experimental procedures and characterization data for new compounds; 1H and 13C NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 37 publications.

  1. Ji Lu, Yuebao Zhang, WenYu Yang, Qianyou Guo, Lu Gao, and Zhenlei Song . Transformation of the B Ring to the C Ring of Bryostatins by Csp3–H Amination and Z to E Isomerization. Organic Letters 2017, 19 (19) , 5232-5235. https://doi.org/10.1021/acs.orglett.7b02510
  2. Paul A. Clarke and Kristaps Ermanis . Synthesis of the C20–C32 Tetrahydropyran Core of the Phorboxazoles and the C22 Epimer via a Stereodivergent Michael Reaction. Organic Letters 2012, 14 (21) , 5550-5553. https://doi.org/10.1021/ol3026523
  3. Haruhiko Fuwa, Naoki Ichinokawa, Kenkichi Noto, and Makoto Sasaki . Stereoselective Synthesis of 2,6-Cis-Substituted Tetrahydropyrans: Brønsted Acid-Catalyzed Intramolecular Oxa-Conjugate Cyclization of α,β-Unsaturated Ester Surrogates. The Journal of Organic Chemistry 2012, 77 (6) , 2588-2607. https://doi.org/10.1021/jo202179s
  4. Yu Lu, Sang Kook Woo, and Michael J. Krische . Total Synthesis of Bryostatin 7 via C–C Bond-Forming Hydrogenation. Journal of the American Chemical Society 2011, 133 (35) , 13876-13879. https://doi.org/10.1021/ja205673e
  5. Paul A. Clarke, Soraia Santos, Nimesh Mistry, Laurence Burroughs, and Alexander C. Humphries . The Asymmetric Maitland−Japp Reaction and Its Application to the Construction of the C1−C19 Bis-pyran Unit of Phorboxazole B. Organic Letters 2011, 13 (4) , 624-627. https://doi.org/10.1021/ol102860r
  6. Bo Wang, T. Matthew Hansen, Ting Wang, Dimao Wu, Lynn Weyer, Lu Ying, Mary M. Engler, Melissa Sanville, Christopher Leitheiser, Mathias Christmann, Yingtao Lu, Jiehao Chen, Nicholas Zunker, Russell D. Cink, Feryan Ahmed, Chi-Sing Lee, and Craig J. Forsyth . Total Synthesis of Phorboxazole A via de Novo Oxazole Formation: Strategy and Component Assembly. Journal of the American Chemical Society 2011, 133 (5) , 1484-1505. https://doi.org/10.1021/ja108906e
  7. Bo Wang, T. Matthew Hansen, Lynn Weyer, Dimao Wu, Ting Wang, Mathias Christmann, Yingtao Lu, Lu Ying, Mary M. Engler, Russell D. Cink, Chi-Sing Lee, Feryan Ahmed, and Craig J. Forsyth . Total Synthesis of Phorboxazole A via de Novo Oxazole Formation: Convergent Total Synthesis. Journal of the American Chemical Society 2011, 133 (5) , 1506-1516. https://doi.org/10.1021/ja1089099
  8. Mathieu Candy, Gérard Audran, Hugues Bienaymé, Cyril Bressy and Jean-Marc Pons. Enantioselective Enzymatic Desymmetrization of Highly Functionalized Meso Tetrahydropyranyl Diols. Organic Letters 2009, 11 (21) , 4950-4953. https://doi.org/10.1021/ol902107g
  9. Doralyn S. Dalisay and Tadeusz F. Molinski. Structure Elucidation at the Nanomole Scale. 2. Hemi-phorboxazole A from Phorbas sp.. Organic Letters 2009, 11 (9) , 1967-1970. https://doi.org/10.1021/ol9004189
  10. Masaru Okutani and Yuji Mori. Conversion of Bromoalkenes into Alkynes by Wet Tetra-n-butylammonium Fluoride. The Journal of Organic Chemistry 2009, 74 (1) , 442-444. https://doi.org/10.1021/jo802101a
  11. Amos B. Smith, III,, Thomas M. Razler,, Jeffrey P. Ciavarri,, Tomoyasu Hirose,, Tomoyasu Ishikawa, and, Regina M. Meis. A Second-Generation Total Synthesis of (+)-Phorboxazole A. The Journal of Organic Chemistry 2008, 73 (4) , 1192-1200. https://doi.org/10.1021/jo7018152
  12. James D. White,, Tae Hee Lee, and, Punlop Kuntiyong. Total Synthesis of Phorboxazole A. 2. Assembly of Subunits and Completion of the Synthesis. Organic Letters 2006, 8 (26) , 6043-6046. https://doi.org/10.1021/ol062531j
  13. Deepak Kumar, Madhu Ganesh, Irishi N N Namboothiri. Metal-mediated reactions of bromoform with electron-rich and electron-deficient carbon-carbon and carbon-hetero atom multiple bonds. Journal of Chemical Sciences 2022, 134 (3) https://doi.org/10.1007/s12039-022-02075-9
  14. Alejandro Gómez-Palomino, Miquel Pellicena, Katrina Krämer, Pedro Romea, Fèlix Urpí, Gabriel Aullón, José M. Padrón. Total synthesis of (+)-herboxidiene/GEX 1A. Organic & Biomolecular Chemistry 2017, 15 (8) , 1842-1862. https://doi.org/10.1039/C7OB00072C
  15. James W. Leahy, Linda Joy Brzezinski. A synthetic approach to the phorboxazoles—synthesis of the exocyclic fragment. Tetrahedron Letters 2016, 57 (42) , 4670-4672. https://doi.org/10.1016/j.tetlet.2016.08.090
  16. Zachary Shultz, James W Leahy. Synthesis of the phorboxazoles—potent, architecturally novel marine natural products. The Journal of Antibiotics 2016, 69 (4) , 220-252. https://doi.org/10.1038/ja.2016.8
  17. Matthew A. Perry, Scott D. Rychnovsky, Nicholas Sizemore. Synthesis of Saturated Tetrahydropyrans. 2014,,, 43-95. https://doi.org/10.1007/978-3-642-41473-2_2
  18. K. Takai. 1.06 Organochromium Reagents. 2014,,, 159-203. https://doi.org/10.1016/B978-0-08-097742-3.00108-7
  19. Bhaskar Chatterjee, Smritilekha Bera, Dhananjoy Mondal. Julia–Kocienski olefination: a key reaction for the synthesis of macrolides. Tetrahedron: Asymmetry 2014, 25 (1) , 1-55. https://doi.org/10.1016/j.tetasy.2013.09.027
  20. Tibor Gracza. Intramolecular Oxycarbonylation in Stereoselective Synthesis. 2013,,, 1-20. https://doi.org/10.1002/9781118596784.ssd015
  21. Eric Stefan, Richard E. Taylor. Ether Transfer Methodology: Application to the Synthesis of Polyketide Natural Products. 2013,,, 1-22. https://doi.org/10.1002/9781118596784.ssd037
  22. Ji Lu, Zhenlei Song, Yuebao Zhang, Zubao Gan, Hongze Li. Prins Cyclization of Bis(silyl) Homoallylic Alcohols to Form 2,6- cis -Tetrahydropyrans Containing a Geometrically Defined Exocyclic Vinylsilane: Efficient Synthesis of Ring B of the Bryostatins. Angewandte Chemie 2012, 124 (22) , 5463-5466. https://doi.org/10.1002/ange.201201323
  23. Ji Lu, Zhenlei Song, Yuebao Zhang, Zubao Gan, Hongze Li. Prins Cyclization of Bis(silyl) Homoallylic Alcohols to Form 2,6- cis -Tetrahydropyrans Containing a Geometrically Defined Exocyclic Vinylsilane: Efficient Synthesis of Ring B of the Bryostatins. Angewandte Chemie International Edition 2012, 51 (22) , 5367-5370. https://doi.org/10.1002/anie.201201323
  24. Liangfeng Fu. Metalation of Oxazoles and Benzoxazoles. 2012,,, 103-154. https://doi.org/10.1007/7081_2012_81
  25. Yu Lu, Michael J. Krische. Bryostatin 7. 2012,,, 103-130. https://doi.org/10.1007/978-3-642-34065-9_5
  26. Punlop Kuntiyong, Tae Hee Lee, Christian L. Kranemann, James D. White. Total synthesis of the marine toxin phorboxazole A using palladium(ii)-mediated intramolecular alkoxycarbonylation for tetrahydropyran synthesis. Organic & Biomolecular Chemistry 2012, 10 (39) , 7884. https://doi.org/10.1039/c2ob25766a
  27. Haruhiko Fuwa. Total Synthesis of Tetrahydropyran-Containing Natural Products Exploiting Intramolecular Oxa-Conjugate Cyclization. HETEROCYCLES 2012, 85 (6) , 1255. https://doi.org/10.3987/REV-12-730
  28. Qin Zang, Shivali Gulab, Bridget L. Stocker, Sylvia Baars, John O. Hoberg. Synthesis of an Acyclic C1-C11 Fragment of Peloruside B. European Journal of Organic Chemistry 2011, 2011 (23) , 4465-4471. https://doi.org/10.1002/ejoc.201100053
  29. David W. Knight. Oxazole and Its Derivatives. 2011,,, 403-458. https://doi.org/10.1002/9783527634880.ch12
  30. Paul A. Clarke, Jason M. Hargreaves, Daniel J. Woollaston, Rosa María Rodríguez Sarmiento. Synthetic studies on the phorboxazoles: a short synthesis of an epi-C23 tetrahydropyran core. Tetrahedron Letters 2010, 51 (36) , 4731-4733. https://doi.org/10.1016/j.tetlet.2010.07.012
  31. Carolina Fontana, Marcelo Incerti, Guillermo Moyna, Eduardo Manta. Insights into the stereoselective BF3-catalyzed hetero Diels–Alder reaction of Garner’s aldehyde with Danishefsky’s diene. Tetrahedron: Asymmetry 2010, 21 (4) , 398-404. https://doi.org/10.1016/j.tetasy.2010.02.028
  32. John A. Soderquist, Qingwei Yao. 9-Bromo-9-borabicyclo[3.3.1]nonane. 2009,,https://doi.org/10.1002/047084289X.rb280.pub2
  33. William P. Griffith. The Chemistry of Ruthenium Oxidation Complexes. 2009,,, 1-134. https://doi.org/10.1007/978-1-4020-9378-4_1
  34. William P. Griffith. Oxidation of Alcohols, Carbohydrates and Diols. 2009,,, 135-172. https://doi.org/10.1007/978-1-4020-9378-4_2
  35. Zhong Jin. Muscarine, imidazole, oxazole and thiazole alkaloids. Natural Product Reports 2009, 26 (3) , 382. https://doi.org/10.1039/b718045b
  36. Krishna C. Majumdar, Pradip Debnath, Brindaban Roy. Metal-Catalyzed Heterocyclization: Formation of Five- and Six-Membered Oxygen Heterocycles through Carbon-Oxygen Bond Forming Reactions. HETEROCYCLES 2009, 78 (11) , 2661. https://doi.org/10.3987/REV-09-656
  37. Neil Henry, Murray N. Robertson, Rodolfo Marquez. Fast and efficient synthesis of the complete LL-Z1640-2 framework. Tetrahedron Letters 2007, 48 (35) , 6088-6091. https://doi.org/10.1016/j.tetlet.2007.06.151

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE