Synthesis of (±)-Secosyrin 1 and a Formal Synthesis of (-) -Secosyrin 1

Organic Letters

Volumn 6, Issue 4, 2004, Pages 465-467

  Donohoe, Timothy J ^a   Fisher, John W ^a   Edwards, Paul J ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; FURAN; FURAN DERIVATIVE; KETONE; SECOSERIN 1; UNCLASSIFIED DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; SECOSYRIN 1;

ALKYLATION; ARTICLE; CHIRALITY; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; PSEUDOMONAS SYRINGAE; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; FURANS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PSEUDOMONAS SYRINGAE; STEREOISOMERISM;

EID: 1342311522     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0362313     Document Type: Article

References (20)

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2. Previous syntheses of secosyrin 1: (a) Mukai, C.; Moharram, S. M.; Hanaoka, M. Tetrahedron Lett. 1997, 38, 2511. (b) Yu, P.; Yang, Y.; Zhang, Z. Y.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 1997, 62, 6359. (c) Carda, M.; Castillo, E.; Rodriguez, S.; Falomir, E.; Marco, J. A. Tetrahedron Lett. 1998, 39, 8895.
3. Previous syntheses of secosyrin 1: (a) Mukai, C.; Moharram, S. M.; Hanaoka, M. Tetrahedron Lett. 1997, 38, 2511. (b) Yu, P.; Yang, Y.; Zhang, Z. Y.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 1997, 62, 6359. (c) Carda, M.; Castillo, E.; Rodriguez, S.; Falomir, E.; Marco, J. A. Tetrahedron Lett. 1998, 39, 8895.
4. Previous syntheses of secosyrin 1: (a) Mukai, C.; Moharram, S. M.; Hanaoka, M. Tetrahedron Lett. 1997, 38, 2511. (b) Yu, P.; Yang, Y.; Zhang, Z. Y.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 1997, 62, 6359. (c) Carda, M.; Castillo, E.; Rodriguez, S.; Falomir, E.; Marco, J. A. Tetrahedron Lett. 1998, 39, 8895.
5. For examples of the Birch reduction of furans in synthesis see: Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullié, M. M. J. Am. Chem. Soc. 1980, 102, 7505. Donohoe, T. J.; Guillermin J.-B.; Walter, D. S. J. Chem. Soc., Perkin Trans. 1 2002, 1369.
6. For examples of the Birch reduction of furans in synthesis see: Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullié, M. M. J. Am. Chem. Soc. 1980, 102, 7505. Donohoe, T. J.; Guillermin J.-B.; Walter, D. S. J. Chem. Soc., Perkin Trans. 1 2002, 1369.
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17. 3) 174.4, 173.6, 86.61, 81.67, 76.40, 75.85, 72.83, 35.47, 34.01, 31.15, 24.46, 22.19, 13.75 ppm.
18. Donohoe, T. J.; Calabrese, A. A.; Guillermin, J.-B.; Walter, D. S. Tetrahedron Lett. 2001, 42, 5841. Donohoe, T. J.; Calabrese, A. A.; Guillermin, J.-B.; Frampton C. S.; Walter, D. J. Chem. Soc., Perkin Trans. 1 2002, 1748.
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20. This argument assumes that compound (-)-6 does not racemize under the dihydroxylation conditions, which seems unlikely.