Oxabicyclo[3.2.1]octenes in organic synthesis: Direct ring opening of oxabicyclo[3.2.1] ring systems with diisobutylaluminum hydride and a silyl ketene acetal - synthesis of the chiral C(19)-C(26) and C(27)-C(32) fragments of scytophycin C

Organic Letters

Volumn 4, Issue 2, 2002, Pages 245-248

  Hunt, Kevin W ^a   Grieco, Paul A ^a  

^a MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ANTINEOPLASTIC AGENT; DIISOBUTYLALUMINUM; ETHYLENE DERIVATIVE; FUSED HETEROCYCLIC RINGS; KETENE; KETONE; ORGANOMETALLIC COMPOUND; PYRAN DERIVATIVE; SCYTOPHYCIN C;

ARTICLE; CHEMISTRY; SYNTHESIS;

ACETALS; ANTINEOPLASTIC AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; ETHYLENES; KETONES; ORGANOMETALLIC COMPOUNDS; PYRANS;

EID: 0037165421     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010253c     Document Type: Article

References (25)

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2. For the use of highly polar media to promote organic reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A. Aldrichimica Acta 1991, 24, 59. Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakurek, V., Ed.; VCH: Basel, 1993; p 133.
3. For the use of highly polar media to promote organic reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A. Aldrichimica Acta 1991, 24, 59. Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakurek, V., Ed.; VCH: Basel, 1993; p 133.
4. For the use of highly polar media to promote organic reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A. Aldrichimica Acta 1991, 24, 59. Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakurek, V., Ed.; VCH: Basel, 1993; p 133.
5. N2′ opening of oxabicyclo[3.2.1]octenes employing diisobutylaluminum hydride see: Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281.
6. (a) For the total synthesis of Scytophycin C, see: Paterson, I.; Watson, C.; Kap-Sun, Y.; Wallace, P. A.; Ward, R. A. J. Org. Chem. 1997, 62, 452. Paterson, I.; Watson, C.; Kap-Sun, Y.; Wallace, P. A.; Ward, R. A. Tetrahedron 1998, 54, 11935; 11955.
7. (a) For the total synthesis of Scytophycin C, see: Paterson, I.; Watson, C.; Kap-Sun, Y.; Wallace, P. A.; Ward, R. A. J. Org. Chem. 1997, 62, 452. Paterson, I.; Watson, C.; Kap-Sun, Y.; Wallace, P. A.; Ward, R. A. Tetrahedron 1998, 54, 11935; 11955.
8. (b) For previous synthetic studies, see: Grieco, P. A.; Speake, J. D.; Yeo, S. K.; Miyashita, M. Tetrahedron Lett. 1998, 39, 1125. Grieco, P. A.; Speake, J. A. Tetrahedron Lett. 1998, 39, 1275.
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25. Attempts to perform the Baeyer-Villiger oxidation on ketone 20 met with no success.