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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 1
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Original Articles

Improved Synthesis of Parent Fused 7-Oxanorbornenes

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Pages 104-110 | Received 21 Jan 2009, Published online: 09 Dec 2009

REFERENCES

  • For leading references, see (a) Cabrera , S. ; Arrayàs , R. G. ; Alonso , I. ; Carretero , J. C. Fe-sulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents . J. Am. Chem. Soc. 2005 , 127 , 17938 – 17947 , and references cited therein; (b) Zhang , W. ; Wang , L.-X. ; Shi , W.-J. ; Zhou , Q.-L. Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with Grignard reagents . J. Org. Chem. 2005 , 70 , 3734 – 3736 , and references cited therein. Reviews; (c) Lautens , M. ; Fagnou , K. ; Hiebert , S. Transition metal–catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes . Acc. Chem. Res. 2003 , 36 , 48 – 58 ; (d) Chiu , P. ; Lautens , M. Using ring-opening strategies of oxabicyclic compounds as a strategy in organic synthesis . Top. Curr. Chem. 1997 , 190 , 1 – 85 . Application in synthesis of drugs; (e) Lautens , M. ; Rovis , T. Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline . Tetrahedron 1999 , 55 , 8967 – 8976 . Application in synthesis of natural products; (f) Enev , V. S. ; Drescher , M. ; Mulzer , J. A non-Diels–Alder approach to the cis-decalin core of branimycin . Org. Lett. 2008 , 10 , 413 – 416 . Synthetic application of substituted fused 7-oxanorbornenes; (g) Lautens , M. ; Fillion , E. New strategy for the stereocontrolled construction of decalins and fused polycycles via a tandem Diels–Alder ring-opening sequence . J. Org. Chem. 1996 , 61 , 7994 – 7995 ; (h) Lautens , M. ; Fillion , E. Exploring the reactivity of dioxacyclic compounds as a route to polysubstituted decalins and fused polycycles . J. Org. Chem. 1998 , 63 , 647 – 656 .
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  • Mixture of 1 and 2 was synthesized in <2% yield over four steps: Maksimović , L. ; Novak , N. ; Eckert-Maksić , M. Synthesis of some novel fused 7-oxanorbornenes . Synth. Comm. 1993 , 23 ( 22 ), 3119 – 3125 .
  • (a) In 37% yield, 1:1 mixture of diastereomers: Lasne , M.-C. ; Ripoll , J.-L. Réactions rétrodiéniques XX: Synthèse et thermolyse éclar de bis-adduits de Diels–Alder: Création d'une triple liason fonctionnalisée par double cycloréversion . Bull. Soc. Chim. Fr. 1986 , 5 , 766 – 770 ; (b) Synthesis of the corresponding ethyl esters in 31% yield, 2:1 mixture of diastereomers: McCulloch , A. W. ; Smith , D. G. ; McInnes , A. G. Influence of Lewis acids on the Diels–Alder reaction, VII: The reaction of furan with propiolate . Can. J. Chem. 1974 , 52 , 1013 – 1018 .
  • Photoinitiated Barton decarboxylation with thiols instead of Bu3SnH: Larsen , D. S. ; Lins , R. J. ; Stoodley , R. J. ; Trotter , N. S. Studies related to carba-pyranoses: A radical decarboxylation approach to monocarba-disaccharides . Org. Biomol. Chem. 2004 , 2 , 1934 – 1942 .

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