Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 11
321
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

An Advanced Intermediate for the Synthesis of (±)‐Pumiliotoxin C and Its Analogues

, , , , , , & show all
Pages 2031-2038 | Received 30 Sep 2003, Published online: 20 Aug 2006

References

  • Daly , J. W. 1998 . Thirty years of discovering arthropod alkaloids in amphibian skin . J. Nat. Prod. , 61 : 162 [PUBMED] [INFOTRIEVE] [CSA]
  • Tokuyama , T. , Tsujita , T. , Shimada , A. , Garraffo , H. M. , Spande , T. F. and Daly , J. W. 1991 . Alkaloids from dendrobatid position frogs: further cis‐decahydroquinolines and 8‐methylindolizidines . Tetrahedron , 47 : 5401 [CROSSREF]
  • Comins , D. L. and Dehghani , A. 1991 . N‐Acyldihydropyridones as synthetic intermediates. A short synthesis of (±) pumiliotoxin C . Tetrahedron Lett. , 32 : 5697 [CROSSREF]
  • Meyers , A. I. and Milot , G. 1993 . α‐Alkylation and stereochemistry of cis and trans‐decahydroquinolines mediated by the formamidine and boc activating groups. Synthesis of pumuliotoxin C . J. Am. Chem. Soc. , 115 : 6652
  • Polniaszek , R. P. and Dillard , L. W. 1992 . Stereospecific total syntheses of decahydroquinoline alkaloids (±)‐195A and (±)‐2‐epi‐195A . J. Org. Chem. , 57 : 4103
  • Mehta , G. and Praveen , M. 1995 . Regioselective Haller–Bauer cleavage in tricyclo [5.2.1.02,6] dec‐8‐3, 10‐dione. A total synthesis of (±) pumiliotoxin C . J. Org. Chem. , 60 : 279
  • Bonin , M. , Royer , J. , Grielson , D. S. and Husson , H. 1986 . Asymmetric synthesis VIII: biogenetically patterned approach to chiral total synthesis of (−)‐pumiliotoxin C . Tetrahedron Lett. , 27 : 1569 For enantiomerically pure pumilitoxin C[CROSSREF]
  • Schultz , A. G. , Mecloskey , P. J. and Court , J. J. 1987 . Enantioselective conversion of anthranilic acid derivatives to chiral cyclohexanes. Total synthesis of (+)‐pumiliotoxin C . J. Am. Chem. Soc. , 109 : 6493
  • Murahashi , S. , Sasao , S. , Saito , E. and Naota , T. 1992 . Ruthenium‐catalyzed hydration of nitriles and transformation of δ‐keto nitriles to ene‐lactams . J. Org. Chem. , 57 : 2521
  • Comins , D. L. and Dehghani , A. 1993 . A short asymmetric synthesis (–)‐pumiliotoxin C . J. Chem. Soc. Chem. Commun. , 24 : 1838 [CROSSREF]
  • Masahiro , T. , Takanobu , A. , Masaki , M. and Keiichiro , F. 1996 . Stereoselective transformation of enantiopure cyclohexenol into cis‐hydrindan. An enantioselective formal total synthetic route to (+)‐pumiliotoxin C . J. Org. Chem. , 61 : 8687 [CROSSREF]
  • Shao , Z. H. , Chen , J. B. , Tu , Y. Q. , Li , L. and Zhang , H. B. 2003 . A facile aminocyclization for the synthesis of pyrrolidine and piperidine derivatives . Chem. Commun. , 15 : 1918 [CROSSREF]
  • Monn , S. 1969 . Lead tetraacetate VI. Stereochemical studies on the formation of bicyclic ethers from alicyclic primary alcohols . J. Org. Chem. , 34 : 288

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.