Asymmetric Total Synthesis of Bacillariolide III, a Marine Oxylipin

Organic Letters

Volumn 6, Issue 3, 2004, Pages 429-432

  Seo, Seung Yong ^a   Jung, Jae Kyung ^c   Paek, Seung Mann ^a   Lee, Yong Sil ^a   Kim, Seok Ho ^a   Lee, Kwang Ok ^a   Suh, Young Ger ^a,b  

^a Seoul National University   (South Korea)

^b Yonsei University   (South Korea)

^c Chungbuk National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BACILLARIOLIDE III; HYDROXYL GROUP; LACTONE DERIVATIVE; PALLADIUM; TOXIC SUBSTANCE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; MOLECULAR DYNAMICS; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

ALDEHYDES; ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; CYCLIZATION; DIATOMS; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 1342306652     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0363366     Document Type: Article

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41. For an example of the nine-membered lactone formation using RCM, see: (a) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653. For selected examples of the synthesis of nine-membered carbo-and heterocycles, see: (b) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548. (c) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299. (d) Bond, S.; Perlmutter, P. Tetrahedron 2002, 58, 1779. (e) Bamford, S. J.; Goubitz, K.; van Lingen, H. L.; Luker, T.; Schenk, H.; Hiemstra, H. J. Chem. Soc., Perkin Trans. 1 2000, 345. (f) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847. (g) Clark, J. S.; Marlin, F.; Nay, B.; Wilson, C. Org. Lett. 2003, 5, 89.
42. For an example of the nine-membered lactone formation using RCM, see: (a) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653. For selected examples of the synthesis of nine-membered carbo-and heterocycles, see: (b) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548. (c) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299. (d) Bond, S.; Perlmutter, P. Tetrahedron 2002, 58, 1779. (e) Bamford, S. J.; Goubitz, K.; van Lingen, H. L.; Luker, T.; Schenk, H.; Hiemstra, H. J. Chem. Soc., Perkin Trans. 1 2000, 345. (f) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847. (g) Clark, J. S.; Marlin, F.; Nay, B.; Wilson, C. Org. Lett. 2003, 5, 89.
43. For an example of the nine-membered lactone formation using RCM, see: (a) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653. For selected examples of the synthesis of nine-membered carbo-and heterocycles, see: (b) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548. (c) Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299. (d) Bond, S.; Perlmutter, P. Tetrahedron 2002, 58, 1779. (e) Bamford, S. J.; Goubitz, K.; van Lingen, H. L.; Luker, T.; Schenk, H.; Hiemstra, H. J. Chem. Soc., Perkin Trans. 1 2000, 345. (f) Harris, P. W. R.; Brimble, M. A.; Gluckman, P. D. Org. Lett. 2003, 5, 1847. (g) Clark, J. S.; Marlin, F.; Nay, B.; Wilson, C. Org. Lett. 2003, 5, 89.