Improved synthesis of parent fused 7-oxanorbornenes

Synthetic Communications

Volumn 40, Issue 1, 2010, Pages 104-110

  Gromov, Alexey ^a   Enev, Valentin ^a   Mulzer, Johann ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Acyl tosylate; Barton decarboxylation; Diepoxynaphthalenes; Fused 7 oxanorbornenes; Saponification

Indexed keywords

7 OXANORBORNENE DERIVATIVE; ESTER DERIVATIVE; FURAN; METHYLPROPIOLATE; NORBORNENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DECARBOXYLATION; DIELS ALDER REACTION; SAPONIFICATION; SYNTHESIS;

EID: 72049112278     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902953323     Document Type: Article

References (14)

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8. Jung, J. C.; Roh, C. H.; Jung, M. H.; Kong, K. K.; Lee, G. S.; Baik, K. H. A photoresist monomer useable in photolithography for producing highly integrated semiconductor elements. Ger. Offen. DE 19940515, March 9, 2000.
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10. 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.
11. (a) In 37% yield, 1:1 mixture of diastereomers: Lasne, M.-C.; Ripoll, J.-L. Réactions rétro-diéniques 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(a);
12. (b) Synthesis of the corresponding ethyl esters in 31% yield, 2:1 mixture of diastereo-mers: 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.
13. 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 decarbox-ylation approach to monocarba-disaccharides. Org. Biomol. Chem. 2004, 2, 1934-1942.
14. (a) For leading references, see 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(a);