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.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Hu Y, Lin G (2008) Modern organic reactions (vol. IV): carbon–carbon bond formation reaction, 1st edn. Chemical Industry Press, Beijing, pp 1–165
WikiPedia (2012) Diels–Alder reaction. http://www.wikipedia.org. Accessed 25 April 2012
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 134:920–923
Taber DF, Nakajima K, Xu M et al (2002) Lactone-directed intramolecular Diels-Alder cyclization: synthesis of trans-dihydroconfertifolin. J Org Chem 67:4501–4504
Evans DA, Starr JT (2002) A cascade cycloaddition strategy leading to the total synthesis of (−)-FR182877. Angew Chem Int Ed 41:1787–1790
Evans DA, Starr JT (2003) A cycloaddition cascade approach to the total synthesis of (−)-FR182877. J Am Chem Soc 125:13531–13540
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 124:4552–4553
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 125:5393–5407
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 48:2580–2583
Maimone TJ, Voica A-F, Baran PS (2008) A concise approach to vinigrol. Angew Chem Int Ed 47:3054–3056
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 67:8348–8352
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 10:1411–1417
Cook SP, Polara A, Danishefsky SJ (2006) The total synthesis of (±)-11-O-Debenzoyltashironin. J Am Chem Soc 128:16440–16441
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 71:995–1001
Hsu D-S, Liao C–C (2003) Total syntheses of sesterpenic acids: refuted (±)-bilosespenes A and B. Org Lett 5:4741–4743
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2014 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Gong, J. (2014). Model Study of Maoecrystal V. In: Total Synthesis of (±)-Maoecrystal V. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-54304-3_2
Download citation
DOI: https://doi.org/10.1007/978-3-642-54304-3_2
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-54303-6
Online ISBN: 978-3-642-54304-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)