Synthesis of Pterocarpan-Type Heterocycles via Oxidative Cycloadditions of Phenols and Electron-Rich Arenes

REFERENCES

• For reviews and leading references, see (a) Harborne , J. B. ; Mabry , T. J. ; Maybry , H. The Flavonoids . New York : Academic Press , 1975 ; (b) Bailey , J. A. ; Mansfield , J. W. (Eds.). Phytoalexins . Wiley : New York , 1982 .
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• (a) 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 ; (b) 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 ; (c) 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 .
   Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• (a) 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 ; (b) 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 ; (c) Gopalsamy , A. ; Balasubramanian , K. Radical cyclization of 4-(o-bromophenoxy)-2 H-1-benzopyrans: An efficient synthesis of pterocarpans . J. Chem. Soc., Chem. Commun. 1988 , 1 , 28 – 29 .
   Google Scholar
• 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 .
   Google Scholar
• (a) 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 ; (b) 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 ; (c) Subburaj , K. ; Murugesh , M. G. ; Trivedi , G. K. ZnCl2 promoted formal (3 + 2) cycloaddition reactions of 2-alkoxy-1,4-benzoquinones with 2 H-1-benzopyrans . Synth. Commun. 1996 , 26 , 2881 – 2893 .
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• (a) 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 ; (b) for preparation of 1b and 1c, see Schuda , P. F. ; Phillips , J. L. A short synthesis of 2H-1-benzopyrans . J. Heterocyclic Chem. 1984 , 21 , 669 – 672 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Kalra , V. K. ; Kukla , A. S. ; Seshadri , T. R. Synthesis of new types of pterocarpans . Indian J. Chem. 1967 , 5 , 607 – 609 .
   Google Scholar
• (a) Suginome , H. Oxygen heterocycles: Maackiain, a new naturally occurring chromanocoumaran . Experientia 1962 , 18 , 161 ; (b) Fukui , K. ; Nakayama , M. Syntheses of pterocarpans, II: Synthesis of(±)-pterocarpin . Bull. Chem. Soc. Jpn. 1969 , 42 , 1408 .
   PubMedGoogle Scholar