Advertisement

Model Study of Maoecrystal V

Chapter
  • 490 Downloads
Part of the Springer Theses book series (Springer Theses)

Abstract

Maoecrystal V is a C-19 diterpenoid natural product with rare caged skeleton. The main difficulties of synthesis were forecasted through structure analysis: (1) construction of highly compact five-membered ring; (2) installing continuous quaternary carbon chiral center; and (3) construction of [2.2.2] bridge ring. For these reasons, total synthesis of Maoecrystal V should conquer enormous challenges in both strategic design and practical reaction exploration. Exploring meritorious methods for basic skeleton construction of Maoecrystal V is the foundation of total synthesis. It is necessary to build up a model in order to provide worthy information for further total synthesis study.

Keywords

Rotary Evaporator Anhydrous Sodium Sulfate Total Synthesis Alder Reaction Liquid Separation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Hu Y, Lin G (2008) Modern organic reactions (vol. IV): carbon–carbon bond formation reaction, 1st edn. Chemical Industry Press, Beijing, pp 1–165Google Scholar
  2. 2.
    WikiPedia (2012) Diels–Alder reaction. http://www.wikipedia.org. Accessed 25 April 2012
  3. 3.
    Deng J, Zhu B, Lu Z et al (2012) Total synthesis of (−)-Fusarisetin A and reassignment of the absolute configuration of its natural counterpart. J Am Chem Soc 134:920–923CrossRefGoogle Scholar
  4. 4.
    Taber DF, Nakajima K, Xu M et al (2002) Lactone-directed intramolecular Diels-Alder cyclization: synthesis of trans-dihydroconfertifolin. J Org Chem 67:4501–4504CrossRefGoogle Scholar
  5. 5.
    Evans DA, Starr JT (2002) A cascade cycloaddition strategy leading to the total synthesis of (−)-FR182877. Angew Chem Int Ed 41:1787–1790CrossRefGoogle Scholar
  6. 6.
    Evans DA, Starr JT (2003) A cycloaddition cascade approach to the total synthesis of (−)-FR182877. J Am Chem Soc 125:13531–13540CrossRefGoogle Scholar
  7. 7.
    Vosburg DA, Vanderwal CD, Sorensen EJ (2002) A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. J Am Chem Soc 124:4552–4553CrossRefGoogle Scholar
  8. 8.
    Vanderwal CD, Vosburg DA, Weiler S et al (2003) An enantioselective synthesis of FR182877 provides a chemical rationalization of its structure and affords multigram quantities of its direct precursor. J Am Chem Soc 125:5393–5407CrossRefGoogle Scholar
  9. 9.
    Tanaka N, Suzuki T, Matsumura T et al (2009) Total synthesis of (−)-FR182877 through tandem IMDA–IMHDA reactions and stereoselective transition-metal-mediated transformations. Angew Chem Int Ed 48:2580–2583CrossRefGoogle Scholar
  10. 10.
    Maimone TJ, Voica A-F, Baran PS (2008) A concise approach to vinigrol. Angew Chem Int Ed 47:3054–3056CrossRefGoogle Scholar
  11. 11.
    Bon DJYD, Banwell MG, Cade IA et al (2011) The total synthesis of (−)-connatusin A, a hirsutane-type sesquiterpene isolated from the fungus Lentinus connatus BCC8996. Tetrahedron 67:8348–8352CrossRefGoogle Scholar
  12. 12.
    Liu X-Y, Cheng H, Li X-H et al (2012) Oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade for the syntheses of (±)-atisine and (±)-isoazitine. Org Biomol Chem 10:1411–1417CrossRefGoogle Scholar
  13. 13.
    Cook SP, Polara A, Danishefsky SJ (2006) The total synthesis of (±)-11-O-Debenzoyltashironin. J Am Chem Soc 128:16440–16441CrossRefGoogle Scholar
  14. 14.
    Yates P, Bhamare NK, Granger T et al (1993) Tandem Wessely oxidation and intramolecular Diels-Alder reactions. IV. The synthesis of (±)-coronafacic acid. Can J Chem 71:995–1001CrossRefGoogle Scholar
  15. 15.
    Hsu D-S, Liao C–C (2003) Total syntheses of sesterpenic acids: refuted (±)-bilosespenes A and B. Org Lett 5:4741–4743CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  1. 1.School of Chemical Biology and BiotechnologyPeking University Shenzhen Graduate School (PKUSZ)ShenzhenPeople’s Republic of China

Personalised recommendations