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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 12
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Original Articles

Efficient Synthesis of Hexahydrocarbazoles

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Pages 1752-1758 | Received 29 Jan 2010, Published online: 29 Apr 2011

REFERENCES

  • (a) Woodward , R. B. ; Cava , M. P. ; Ollis , W. D. ; Hunger , A. ; Daeniker , H. U. ; Schenker , K. The total synthesis of strychnine . J. Am. Chem. Soc. 1954 , 76 , 4749 – 4751 ; (b) Saxton , J. E. In The Alkaloids of the Aspidospermine Group; G. A. Cordell (Ed.); Academic Press: New York, 1998; vol. 51, p. 1 ; (c) Ando , M. ; Büchi , G. ; Ohnuma , T. The total synthesis of (±)-vindoline . J. Am. Chem. Soc. 1975 , 97 , 6880 ; (d) Zhou , S.-Z. ; Bommezijn , S. ; Murphy , J. A. Formal total synthesis of (±)-vindoline by tandem radical cyclization . Org. Lett. 2002 , 4 , 443 , and references therein ; (d) Choi , Y. ; Ishikawa , H. ; Velcicky , J. ; Elliott , G. I. ; Miller , M. M. ; Boger , D. L. Total synthesis of (−)- and ent-(+)-vindoline . Org. Lett. 2005 , 20 , 4539 – 4542 ; (e) Benchekroun-Mounir , N. ; Dugat , D. ; Gramain , J. C. A short synthesis of (±)-N-benzyl aspidospermidine . Tetrahedron Lett. 1992 , 33 , 4001 – 4004 .
  • (a) Gioia , C. ; Hauville , A. ; Bernardi , L. ; Fini , F. ; Ricci , A. Organocatalytic asymmetric Diels–Alder reactions of 3-vinylindoles . Angew. Chem., Int. Ed. 2008 , 47 , 9236 ; (b) Fu , J.-M. Preparation of arylsulphonyl-substituted tetrahydro- and hexahydrocarbazolamines as 5-HT6 receptor ligands . WO Patent 2003030901 , 2003 ; (c) Fernandez , F. ; Garcia-Mera , X. ; Rodriguez , G. ; Urrutia , A. New hexahydrocarbazoles and spiro indoles and their affinity for D2 dopamine and 5-HT2A serotonin receptors . Chem. Pharm. Bull. 1999 , 47 , 1006 ; (d) Rodriguez , J. G. ; Urrutia , A. Synthesis of sterically hindered 4a,9a-disubstituted 1,2,3,4,4a,9a-hexahydrocarbazoles from 4a-methyl-1,2,3,4-tetrahydro-4aH-carbazole with organolithium reagents . Tetrahedron 1998 , 54 , 15613 ; (d) McCarthy , C. ; Jones , K. Indole alkaloid synthesis: A stereospecific preparation of functionalized cis-hexahydrocarbazoles . J. Chem. Soc., Chem. Comm. 1989 , 22 , 1717 ; (e) Borch , R. F. ; Newell , R. G. Novel synthesis of 2-oxo-1,2,3,4-tetrahydrocarbazoles . J. Org. Chem. 1973 , 38 , 2729 – 2730 .
  • (a) Hyde , A. M. ; Buchwald , S. L. Palladium-catalyzed γ-arylation of β,γ-unsaturated ketones: Application to a one-pot synthesis of tricyclic indolines. Angew. Chem. Int. Ed. 2008, 47, 177–180; (b) Beniazza , R. ; Dunet , J. ; Robert , F. ; Schenk , K. ; Landais , Y. Efficient synthetic approaches to common indole alkaloids. Org. Lett. 2007, 9, 3913–3916; (c) Heureux , N. ; Wouters , J. ; Mark , I. E. Sequential acid/base-catalyzed polycyclization of the tryptamine derivatives: A rapid access to Büchi's ketone. Org. Lett. 2005, 7, 5245–5248; (d) Marcos , I. S. ; Moro , R. F. ; Costales , I. ; Escola , M. A. ; Basabe , P. ; Diez , D. ; Urones , J. G. Synthesis of hexahydrocarbazoles by cyclisation of 3-(but-3-enyl) indole derivatives. Tetrahedron 2009, 65, 10235–10242; (e) Majumdar , K. C. ; Kundu , U. K. ; Das , U. ; Jana , N. K. ; Roy , B. N-Iodosuccinimide, an effective reagent for regioselective heterocyclization of o-cyclohex-2′-enylanilines for the synthesis of hexahydrocarbazoles. Can. J. Chem. 2005, 83, 63–67; (f) Khan , T. A. ; Tripoli , R. ; Crawford , J. J. ; Martin , C. G. ; Murphy , J. A. Diethylphosphine oxide (DEPO): High-yielding and facile preparation of indolones in water. Org. Lett. 2003, 5, 2971–2974.
  • Labadie , S. S. ; Parmer , C. Facile synthesis of spirocyclic oxindole, azaoxindole, and dihydroisoquinolone . Synth. Commun. 2011 , 41 , 1742 – 1751 .
  • (a) Rupprecht , K. M. ; Boger , J. ; Hoogsteen , K. ; Nachbar , R. B. ; Springer , J. P. Controlling the stereochemistry of the ring junction in hexahydrodibenzofurans . J. Org. Chem. 1991 , 56 , 6180 – 6188 ; (b) Hamilton , C. J. ; Fairlamb , A. H. ; Egleston , I. M. Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine, a time-dependent inhibitor of trypanothione reductase . J. Chem. Soc. Perkin Trans. I 2002 , 1115 – 1123 .
  • Current name and affiliation for Christa Parmer: Christa Tatyosian, Bio-Rad Laboratories, Hercules, California, USA.

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