Synthetic Studies on Erythrina Alkaloids: Formal Total Synthesis of (+)-3-Demethoxyerythratidinone

REFERENCES

• Tanaka , H. ; Tanaka , T. ; Etoh , H. ; Goto , S. ; Terada , Y. Two new erythrinan alkaloids from Erythrina x bidwillii . Heterocycles 1999 , 51 , 2759 – 2764 .
   Web of Science ®Google Scholar
• Dyke , S. F. ; Quessy , S. N. Erythrina and related alkaloids . In The Alkaloids ; R. G. A. Rodrigo (Ed.); Academic Press : New York , 1981 ; vol. 18 , pp. 1 – 98 .
   Google Scholar
• Chawla , A. S. ; Kapoor , V. K. Erythrina alkaloids . In The Alkaloids: Chemical and Biological Perspectives ; S. W. Pelletier (Ed.); Pergamon : New York , 1995 ; vol. 9 , pp. 86 – 153 .
   Google Scholar
• Padwa , A. ; Hennig , R. ; Kappe , C. O. ; Reger , T. S. A triple-cascade sequence as a strategy for the construction of the erythrinan skeleton . J. Org. Chem. 1998 , 63 , 1144 – 1155 , and references cited therein .
   Web of Science ®Google Scholar
• Lete , E. ; Egiarte , A. ; Sotomayor , N. ; Vicente , T. ; Villa , M.-J. Synthesis of pyrroloisoquinolones via organolithium additions to N-phenethylsuccinimides . Synlett 1993 , 41 – 42 .
   Web of Science ®Google Scholar
• Rigby , J. H. ; Hughes , R. C. ; Heeg , M. J. Endo-selective cyclization pathways in the intramolecular Heck reaction . J. Am. Chem. Soc. 1995 , 117 , 7834 – 7835 .
   Web of Science ®Google Scholar
• Lee , Y. S. ; Kang , D. W. ; Lee , S. J. ; Park , H. Asymmetric synthesis of both enantiomers of pyrrolidinoisoquinoline derivatives from L-malic acid and L-tartaric acid . J. Org. Chem. 1995 , 60 , 7149 – 7152 .
   Web of Science ®Google Scholar
• Lee , Y. S. ; Kang , D. W. ; Lee , S. J. ; Park , H. Stereoselective synthesis of an isoquinolinopyrrolidinone by acyliminium ion cyclization of chiral hydroxylactams . Synth. Commun. 1995 , 25 , 1947 – 1956 .
   Web of Science ®Google Scholar
• Manteca , I. ; Sotomayor , N. ; Villa , M.-J. ; Lete , E. Tandem carbophilic addition-N-acyliminium ion cyclization for the synthesis of functionalized pyrrolo[2,1-a]isoquinolones: Key intermediates for the preparation of Erythrina-type alkaloids . Tetrahedron Lett. 1996 , 37 , 7841 – 7844 .
   Web of Science ®Google Scholar
• Lee , J. Y. ; Lee , Y. S. ; Chung , B. Y. ; Park , H. Asymmetric synthesis of both enantiomers of novel tetracyclic heterocycle, furo[3’,2':2,3]pyrrolo[2,1-a]isoquinoline derivative via a diastereoselective N-acyliminium ion cyclization . Tetrahedron 1997 , 53 , 2449 – 2458 .
   Web of Science ®Google Scholar
• Padwa , A. ; Hennig , R. ; Kappe , C. O. ; Reger , T. S. A triple-cascade sequence as a strategy for the construction of the erythrinane skeleton . J. Org. Chem. 1998 , 63 , 1144 – 1155 .
   Web of Science ®Google Scholar
• Rigby , J. H. ; Deur , C. ; Heeg , M. J. Synthetic studies on the Erythrina alkaloids: Preparation of (±)-2-epi-erythrinitol . Tetrahedron Lett. 1999 , 40 , 6887 – 6890 .
   Web of Science ®Google Scholar
• Katritzky , A. R. ; Mehta , S. ; He , H.-Y. Syntheses of pyrrolo- and indoloisoquinolinones by intramolecular cyclizations of 1-(2-arylethyl)-5-benzotriazolylpyrrolidin-2-ones and 3-benzotriazolyl-2-(2-arylethyl)-1-isoindolinones . J. Org. Chem. 2001 , 66 , 148 – 152 .
   PubMed Web of Science ®Google Scholar
• Garcia , E. ; Arrasate , S. ; Ardeo , A. ; Lete , E. ; Sotomayor , N. Enantioselective synthesis of pyrrolo[2,1-a]isoquinolones via stereocontrolled N-acyliminium ion cyclisations . Tetrahedron Lett. 2001 , 42 , 1511 – 1513 .
   Web of Science ®Google Scholar
• Lee , H. I. ; Cassidy , M. P. ; Rashatasakhon , P. ; Padwa , A. Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (±)-epi-zephyranthine . Org. Lett. 2004 , 6 , 2189 – 2192 .
   PubMed Web of Science ®Google Scholar
• Padwa , A. ; Wang , Q. Synthesis of the tetracyclic framework of the Erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans . J. Org. Chem. 2006 , 71 , 7391 – 7402 .
   PubMed Web of Science ®Google Scholar
• Zhang , F. ; Simpkins , N. S. ; Blake , A. J. New approaches for the synthesis of erythrinan alkaloids . Org. Biomol. Chem. 2009 , 7 , 1963 – 1979 .
   PubMed Web of Science ®Google Scholar
• Barton , D. H. R. ; Gunatilaka , A. A. L. ; Letcher , R. M. ; Lobo , A. M. F. T. ; Widdowson , D. A. Phenol oxidation and biosynthesis, part XXII: The alkaloids of Erythrina lysistemon, E. abyssinica, E. poeppigiana, E. fusca, and E. lithosperma: Structure of erythratidine. J. Chem. Soc., Perkin Trans. 1973, 1, 874–880.
   Google Scholar
• Tsuda , Y. ; Nakai , A. ; Ito , K. ; Suzuki , F. ; Haruna , M. Synthesis of Erythrina and related alkaloids, part 10: Synthesis of (±)-3-demethoxyerythratidinone, an alkaloid of Erythrina lithosperma Blume . Heterocycles 1984 , 22 , 1817 – 1820 .
   Web of Science ®Google Scholar
• Hosoi , S. ; Ishida , K. ; Tsuda , Y. Synthesis of Erythrina and related alkaloids, XXXVII: Chiral synthesis of enantio-type erythrinan alkaloids utilizing asymmetric acylation and kinetic resolution of diastereomers . Chem. Pharm. Bull. 1992 , 40 , 3115 – 3117 .
   Web of Science ®Google Scholar
• Tsuda , Y. T. ; Hosai , S. ; Ishida , K. ; Sangai , M. Synthesis of Erythrina and related alkaloids. XLII: Chiral synthesis of Erythrina alkaloids (2): Synthesis of enantio-type erythrinan alkaloids utilizing asymmetric acylation and kinetic resolution of diastereomers . Chem. Pharm. Bull. 1994 , 42 , 204 – 213 .
   Web of Science ®Google Scholar
• Danishefsky , S. J. ; Panek , J. S. Total synthesis of (±)-3-demethoxyerythratidinone: Demonstration of a radical cyclization route to a site-specific enol derivative . J. Am. Chem. Soc. 1987 , 109 , 917 – 918 .
   Web of Science ®Google Scholar
• Irie , H. ; Shibata , K. ; Matsuno , K. ; Zhang , Y. Syntheses of an alkaloid, (±)-3-demethoxyerythratidinone . Heterocycles 1989 , 29 , 1033 – 1035 .
   Web of Science ®Google Scholar
• Wasserman , H. H. ; Amici , R. M. The chemistry of vicinal tricarbonyls: A total synthesis of (±)-3-demethoxyerythratidinone . J. Org. Chem. 1989 , 54 , 5843 – 5844 .
   Web of Science ®Google Scholar
• Tsuda , Y. ; Sakai , Y. ; Nakai , A. ; Kaneko , M. ; Ishiguro , Y. ; Isobe , K. ; Taga , J. ; Sano , T. Synthesis of Erythrina and related alkaloids, XXII: Intramolecular cyclization approach (1): New synthetic route to erythrinan and related heterocycles and synthesis of (±)-3-demethoxyerythratidinone . Chem. Pharm. Bull. 1990 , 38 , 1462 – 1472 .
   Web of Science ®Google Scholar
• Ishibashi , H. ; Sato , T. ; Takahashi , M. ; Hayashi , M. ; Ishikawa , K. ; Ikeda , M. A concise total synthesis of (±)-3-demethoxyerythratidinone based on an acid-promoted double cyclization of α-sulfinylacetamides . Chem. Pharm. Bull. 1990 , 38 , 907 – 911 .
   Web of Science ®Google Scholar
• Cassayre , J. ; Quiclet-Sire , B. ; Saunier , J.-B. ; Zard , S. Z. Nickel powder–promoted 5-endo radical cyclizations: A concise approach to Erythrina alkaloids . Tetrahedron Lett. 1998 , 39 , 8995 – 8998 .
   Web of Science ®Google Scholar
• Allin , S. M. ; Streetley , G. B. ; Slater , M. ; James , S. L. ; Martin , W. P. A formal asymmetric synthesis of both enantiomers of the Erythrina alkaloid 3-demethoxyerythratidinone . Tetrahedron Lett. 2004 , 45 , 5493 – 5496 .
   Web of Science ®Google Scholar
• Wang , Q. ; Padwa , A. Synthesis of the Erythrina alkaloid 3-demethoxyerythratidinone: Novel acid-induced rearrangements of its precursors . Org. Lett. 2006 , 8 , 601 – 604 .
   PubMed Web of Science ®Google Scholar
• Gao , S. ; Tu , Y. Q. ; Hu , X. ; Wang , S. ; Hua , R. ; Jiang , Y. ; Zhao , Y. ; Fan , X. ; Zhang , S. General and efficient strategy for erythrinan and homoerythrinan alkaloids: Syntheses of (±)-3-demethoxyerythratidinone and (±)-erysotramidine . Org. Lett. 2006 , 8 , 2373 – 2376 .
   PubMed Web of Science ®Google Scholar
• Zhang , F. ; Simpkins , N. S. ; Wilson , C. An enantiospecific synthesis of (+)-demethoxyerythratidinone from (S)-malic acid: Key observations concerning the diastereocontrol in malic acid–derived N-acyliminium ion cyclisations . Tetrahedron Lett. 2007 , 48 , 5942 – 5947 .
   Web of Science ®Google Scholar
• Maryanoff , B. E. ; Zhang , H.-C. ; Cohen , J. H. ; Turchi , I. J. ; Maryanoff , C. A. Cyclizations of N-acyliminium ions . Chem. Rev. 2004 , 104 , 1431 – 1628 .
   PubMed Web of Science ®Google Scholar
• Huang , P.-Q. Asymmetric synthesis of hydroxylated pyrrolidines, piperidines, and related bioactive compounds: From N-acyliminium chemistry to N-α-carbanion chemistry . Synlett 2006 , 1133 – 1149 .
   Web of Science ®Google Scholar
• Speckamp , W. N. ; Moolenaar , M. J. New developments in the chemistry of N-acyliminium ions and related intermediates . Tetrahedron 2000 , 56 , 3817 – 3856 .
   Web of Science ®Google Scholar
• Speckamp , W. N. ; Hiemstra , H. Intramolecular reactions of N-acyliminium intermediates. Tetrahedron 1985, 41, 4367–4416.
   Web of Science ®Google Scholar
• Lee , H. K. ; Cassidy , M. P. ; Rashatasakhon , P. ; Padwa , A. Efficient synthesis of (±)-erysotramidine using an NBS-promoted cyclization reaction of a hexahydroindolinone derivative . Org. Lett. 2003 , 5 , 5067 – 5070 .
   PubMed Web of Science ®Google Scholar
• Irlend , R. E. ; Norbeck , D. W. Application of the Swern oxidation to the manipulation of highly reactive carbonyl compounds . J. Org. Chem. 1985 , 50 , 2198 – 2200 .
   Web of Science ®Google Scholar
• Tsuji , J. New synthetic reactions catalyzed by palladium complexes . Pure Appl. Chem. 1986 , 58 , 869 – 878 .
   Web of Science ®Google Scholar
• Hughes , G. ; Lautens , M. ; Wen , C. Use of γ-carboxy-α, β-unsaturated aldehydes as synthetic equivalents of β,γ-unsaturated aldehydes in a novel stereoselective approach to diketides . Org. Lett. 2000 , 2 , 107 – 110 .
   PubMed Web of Science ®Google Scholar
• Pellissier , H. ; Michellys , P. ; Santelli , M. Regiochemistry of Wacker-type oxidation of vinyl group in the presence of neighboring oxygen functions . Tetrahedron 1997 , 53 , 7577 – 7586 .
   Web of Science ®Google Scholar
• Ley , S. V. ; Norman , J. ; Griffith , W. P. ; Marsden , S. P. ; Tetrapropylammonium perruthenate, , TPAP: A catalytic oxidant for organic synthesis . Synthesis 1994 , 639 – 666 .
   Web of Science ®Google Scholar
• Coulsen , D. R. A new synthesis of methyl ketones. Tetrahedron Lett. 1964 , 45 , 3323 – 3326 .
   Google Scholar