Synthesis of pterocarpan-type heterocycles via oxidative cycloadditions of phenols and electron-rich arenes

Synthetic Communications

Volumn 39, Issue 21, 2009, Pages 3845-3855

  Mohr, Amber L ^a   Lombardo, Vincent M ^a   Arisco, Teresa M ^a   Morrow, Gary W ^a  

^a UNIVERSITY OF DAYTON   (United States)

Author keywords

Carbapterocarpan; Cycloaddition; Hypervalent iodine reagent; Oxidation; Phenol; Pterocarpan; Quinone monoacetal

Indexed keywords

HETEROCYCLIC COMPOUND; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PTEROCARPAN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ELECTRON; IONIZATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 70349906755     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902838961     Document Type: Article

References (23)

1. Harborne, J. B.; Mabry, T. J.; Maybry, H. The Flavonoids. New York: Academic Press, 1975
2. Bailey, J. A.; Mansfield, J. W. (Eds.). Phytoalexins. Wiley: New York, 1982.
3. Selvam, C; Jachak, S. M.; Oli, R. G.; Thilagavathi, R.; Chakraborti, A. K.; Bhutani, K. K. A new cyclooxygenase (COX) inhibitory pterocarpan from Indigofera aspalathoides. Tetrahedron Lett. 2004, 45, 4311-4314.
4. Maurich, T.; Iorio, M.; Chimenti, D.; Turchi, G. Erybraedin C and bitucarpin A induced apoptosis in human colon adenocarcinoma cell lines. Chem. Biol. Interact. 2006, 159, 104-116.
5. Lee, J. H.; Lee, B. W.; Kim, J. H.; Jeong, T.-S.: Kim, M. J.; Lee, W. S.; Park, K. H. LDL-antioxidant pterocarpans from roots of Glycine max (L.) Merr. J. Agric. Food Chem. 2006, 54, 2057-2063.
6. Engler, T. A.; Letavic, M. A.; Lyengar, R.; LaTessa, K. O.; Reddy, J. P. Asymmetric reactions of 2-methoxy-1,4-benzoquinones with styrenyl systems: Enantioselective syntheses of 8-aryl-3-methoxybicyclo[4.2.0]oct-3-ene-2,5- diones, 7-aryl-3-hydroxybicyclo[3.2.1]oct-3-ene-2,8-diones, 2-aryl-6-methoxy-2, 3-dihydrobenzofuran-5-ols, and pterocarpans. J. Org. Chem. 1999, 64, 2391-2405
7. Engler, T. A.; LaTessa, K. O.; Iyengar, R.; Chai, W.; Agrios, K. Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogs. Bioorg. Med. Chem. 1996, 4, 1755-1769
8. Engler, T. A.; Lynch, K. O. Jr.; Reddy, J. P.; Gregory, G. S. Synthetic pterocarpans with anti-HIV activity. Bioorg. Med. Chem. Lett. 1993, 3, 1229-1232.
9. da Silva, A. J. M.; Coelho, A. L.; Simas, A. B. C; Moraes, R. A. M.; Pinheiro, D. A.; Fernandes, F. F. A.; Arruda, E. Z.; Costa, P. R. R.; Melo, P. A. Synthesis and pharmacological evaluation of prenylated and benzylated pterocarpans against snake venom. Bioorg. Med. Chem. Lett. 2004, 14, 431-435.
10. Miki, Y.; Fujita, R.; Matsushita, K. Oxidative rearrangement of pentaalkoxy-chalcones with phenyliodine(III) bis(trifluoroacetate) (PIFA): Synthesis of (±)-10-bromopterocarpin and (±)-pterocarpin. J. Chem. Soc, Perkin Trans. 1 1998, 16, 2533-2536
11. Van Aardt, T. G.; Van Heerden, P. S.; Ferreira, D. The first direct synthesis of pterocarpans via aldol condensation of phenylacetates with benzaldehydes. Tetrahedron Lett. 1998, 39, 3881-3884
12. Gopalsamy, A.; Balasubramanian, K. Radical cyclization of 4-(o-bromophenoxy)-2H-1-benzopyrans: An efficient synthesis of pterocarpans. J. Chem. Soc, Chem. Commun. 1988, 1, 28-29.
13. Lichtenfels, R. A.; Coelho, A. L.; Costa, P. R. R. Total synthesis of pterocarpan: (±)-Neorautenane. J. Chem. Soc, Perkin Trans. 1 1995, 7, 949-951.
14. Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. Formal 2 + 2 and 3 + 2 cycloaddition reactions of 2H-1-benzopyrans with 2-alkoxy-1,4-benzoquinones: Regioselective synthesis of pterocarpans. J. Org. Chem. 1990, 55, 1248
15. Subburaj, K.; Murugesh, M. G.; Trivedi, G. K. Regioselective total synthesis of edulane and its angular analog. J. Chem. Soc, Perkin Trans. 1 1997, 12, 1875-1878
16. Subburaj, K.; Murugesh, M. G.; Trivedi, G. K. ZnCl2 promoted formal (3 + 2) cycloaddition reactions of 2-alkoxy-1,4-benzoquinones with 2H-1-benzopyrans. Synth. Commun. 1996, 26, 2881-2893.
17. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. Mechanistic aspects and synthetic applications of the electrochemical and iodobenzene bis (trifluoroacetate) oxidative 1,3-cycloadditions of phenols and electron-rich styrene derivatives. J. Org. Chem. 1992, 57, 2135-2143
18. For preparation of 1a, see Zhang, X.; Thimmaiah, M.; Fang, S. Simple and efficient synthesis of 4,7-dimethoxy-1(H)-indene. Synth. Commun. 2007, 37, 1873-1877
19. Schuda, P. F.; Phillips, J. L. A short synthesis of 2H-1-benzopyrans. J. Heterocyclic Chem. 1984, 21, 669-672
20. For preparation of 4b and 4c, see Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. Hypervalent iodine oxidation of p-alkoxyphenols and related compounds: A general route to p-benzoquinone monoacetals and spiro lactones. J. Org. Chem. 1987, 52, 3927-3930.
21. Kalra, V. K.; Kukla, A. S.; Seshadri, T. R. Synthesis of new types of pterocarpans. Indian J. Chem. 1967, 5, 607-609.
22. Suginome, H. Oxygen heterocycles: Maackiain, a new naturally occurring chromanocoumaran. Experientia 1962,18, 161
23. Fukui, K.; Nakayama, M. Syntheses of pterocarpans, II: Synthesis of(±)-pterocarpin. Bull. Chem. Soc. Jpn. 1969, 42, 1408.