Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 9
378
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Reductive Studies on 3-Oxidopyrylium-alkene [5 + 2] Cycloadducts: Access to Some Hydroxy Cycloheptenoids

, , , , &
Pages 1326-1337 | Received 12 Dec 2009, Published online: 30 Mar 2011

REFERENCES

  • (a) Hendrickson , J. B. ; Farina , J. S. A new 7-ring cycloaddition reaction . J. Org. Chem. 1980 , 45 , 3359 ; (b) Sammes , P. G. ; Street , L. J. Intramolecular cycloadditions with oxidopyrylium ylides . Chem. Commun. 1982 , 1056 ; (c) Sammes , P. G. ; Street , L. J. Preparation and properties of some phytotoxic 2-benzyloxy-8-oxabicyclo [3.2.1] octane derivatives . J. Chem. Soc. , Perkin Tran . 1 1983 , 2729 ; (d) Sammes , P. G. ; Street , L. J. The preparation and some reactions of 3-oxidopyrylium . J. Chem. Soc. , Perkin Tran . 1 1983 , 1261 ; (e) Sammes , P. G. ; Street , L. J. Total synthesis of (±)-β-bulnesene, (±)-cryptofauronol, (±)-fauronyl acetate, and (±)-valeranone . Chem. Commun. 1983 , 666 ; (f) Sammes , P. G. ; Whitby , R. J. On the preparation of 2-benzopyrylium-4-oxide and its cycloaddition properties . Chem. Commun. 1984 , 702 ; (g) Bromidge , S. M. ; Sammes , P. G. ; Street , L. J. Total synthesis of (±)-β-bulnesene via intramolecular cycloaddition of a 2-substituted 3-oxidopyrylium . J. Chem. Soc. , Perkin Trans . 1 1985 , 1725 ; (h) Sammes , P. G. ; Whitby , R. J. Synthesis of (±)-cryptofauronol and related valerane sesquiterpenes via rearrangement of bicyclo [5.3.0] decane precursors . J. Chem. Soc. , Perkin Trans. 5 1986 , 281 ; (i) Archer , D. A. ; Bromidge , S. ; Sammes , P. G. Studies on a new route to (±)-copaene and (±)-ylangene . J. Chem. Soc. , Perkin Trans . 1 1988 , 3223 .
  • (a) Sammes , P. G. Recent studies on 3-oxidopyrylium and its derivatives . Gazz. Chim. Ital. 1986 , 116 , 109 ; (b) Ohkata , K. ; Akiba , K. Y. Cycloadditions and reactions of oxa-aromatics with nucleophiles . Adv. Heterocycl. Chem. 1996 , 65 , 283 .
  • (a) Singh , V. ; Krishna , U. M. ; Vikrant ; Trivedi , G. K. Cycloaddition of oxidopyrylium species in organic synthesis . Tetrahedron 2008 , 64 , 3405 ; (b) Radhakrishnan , K. V. Heterocycles via pyrylium and pyridinium betaines . Top. Heterocycl. Chem. 2008 , 13 , 71 .
  • (a) Nose , A. ; Kudo , T. Reduction with sodium borohydride–transition metal salt systems, I: Reduction of aromatic nitro compounds with the sodium borohydride–nickelous chloride system . Chem. Pharm. Bull. 1981 , 29 , 1159 ; (b) Ipaktschi , J. Reduction of oximes with sodium borohydride in the presence of transition metal compounds . Chem. Ber. 1984 , 117 , 856 ; (c) Sarma , D. N. ; Sharma , R. P. Reductive removal of allylic functional groups by nickel boride . Tetrahedron Lett. 1985 , 26 , 2581 – 2584 ; (d) Ganem , B. ; Osby , J. O. Synthetically useful reactions with metal boride and aluminide catalysts . Chem. Rev. 1986 , 86 , 763 ; (e) Back , T. G. ; Yang , K. ; Krouse , H. R. Desulfurization of benzo- and dibenzothiophenes with nickel boride . J. Org. Chem. 1992 , 57 , 1986 ; (f) Back , T. G. ; Baron , D. L. ; Yang , K. Desulfurization with nickel and cobalt boride: Scope, selectivity, stereochemistry, and deuterium-labeling studies . J. Org. Chem. 1993 , 58 , 2407 , and references cited therein ; (g) Choi , J. ; Yoon , N. M. An excellent nickel boride catalyst for the selective hydrogenation of olefins . Synthesis 1996 , 597 ; (h) Khurana , J. M. ; Gogia , A. Synthetically useful reactions with nickel boride . Org. Prep. Proced. Int. 1997 , 29 , 1 ; (i) Khurana , J. M. ; Ray , A. ; Singh , S. Deoxygenation of sulfoxides and selenoxides with nickel boride . Tetrahedron Lett. 1998 , 3829 ; (j) Khurana , J. M. ; Chauhan , S. Rapid reduction of carbonyls with nickel boride at ambient temperature . Synth. Commun. 2001 , 31 , 3485 ; (k) White , R. D. ; Wood , J. L. Progress toward the total synthesis of kalihinane diterpenoids . Org. Lett. 2001 , 3 , 1825 ; (l) Khurana , J. M. ; Kukreja , G. Rapid reduction of nitriles to primary amines with nickel boride at ambient temperature . Synth. Commun. 2002 , 32 , 1265 .
  • Khurana , J. M. ; Sharma , P. Chemoselective reduction of α,β-unsaturate aldehydes, ketones, carboxylic acids, and esters with nickel boride in methanol–water . Bull. Chem. Soc. Jpn. 2004 , 77 , 549 .
  • (a) Krishna , U. M. ; Deodhar , K. D. Trivedi, G. K. Asymmetric oxidopyrylium–alkene [5 + 2] cycloaddition: A divergent approach for the synthesis of enantiopure oxabicyclo[5.4.0]undecanes . Tetrahedron 2004 , 60 , 4829 ; (b) Krishna , U. M. ; Deodhar , K. D. ; Trivedi , G. K. ; Mobin , S. M. Novel route to functionalized cyclooctanoids via [5 + 3] cycloaddition . J. Org. Chem. 2004 , 69 , 967 ; (c) Krishna , U. M. ; Trivedi , G. K. Studies towards the synthesis of FCRR toxin: An expeditious entry into 7–5–6 ring systems via [5 + 2] oxidopyrylium–alkene cycloaddition . Tetrahedron Lett. 2004 , 45 , 257 ; (d) Krishna , U. M. ; Srikanth , G. S. C. ; Trivedi , G. K. ; Deodhar , K. D. Asymmetric oxidopyrylium–alkene [5 + 2] cycloaddition: Synthesis of enantiopure oxa-bridged bicyclo[5.4.0]undecanes . Synlett 2003 , 2383 ; (e) Yadav , A. A. ; Sarang , P. S. ; Wannere , C. S. ; Trivedi , G. K. ; Salunkhe , M. M. Dipolar cycloaddition of dicyclopentadiene with 3-oxidopyrylium betaine: An entry into methano-bridged 5–6–7-fused ring system . Synthesis 2008 , 12 , 1883 .
  • The endo-isomers show a coupling constant (J) in the range of 5–7 Hz for the bridgehead protons whereas the corresponding protons in the exo-isomer show a coupling constant in the range of 0–2 Hz. For further discussions , see Sammes , P. G. ; Street , L. J. J. Chem. Res., synop. 1984 , 196 .
  • (a) Chiu , P. ; Lautens , M. Using ring-opening reactions in the synthesis of natural products . Top. Curr. Chem. 1997 , 190 , 1 – 85 ; (b) House , H. O. ; Ro , R. S. The stereochemistry of elimination reactions involving halohydrin derivatives and metals . J. Am. Chem. Soc. 1958 , 80 , 182 .

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.