Total synthesis of (±)-methyl rishirilide B

Organic Letters

Volumn 1, Issue 2, 1999, Pages 335-336

  Hauser, Frank M ^a   Xu, Yong Jin ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA 2 MACROGLOBULIN; ANTHRACENE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FIBRINOLYTIC AGENT; METHYL RISHIRILIDE B; RISHIRILIDE B;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; HYDROLYSIS; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

ALPHA-MACROGLOBULINS; ANTHRACENES; FIBRINOLYTIC AGENTS; HYDROLYSIS; INDICATORS AND REAGENTS; STEREOISOMERISM; STREPTOMYCES;

EID: 0033614860     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9906561     Document Type: Article

References (13)

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3. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tomassi, R. A. J. Org. Chem. 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722.
4. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tomassi, R. A. J. Org. Chem. 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722.
5. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tomassi, R. A. J. Org. Chem. 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722.
6. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tomassi, R. A. J. Org. Chem. 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722.
7. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tomassi, R. A. J. Org. Chem. 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722.
8. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tomassi, R. A. J. Org. Chem. 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722.
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10. Had 5b undergone iodo-lactonization, the product would have had three substituents with 1,3-diaxial relationships, which would be highly unfavorable. Furthermore, calcuations (Cache) indicate that there is a substantial difference (6.39 kcal/mol) in relative energy between 5a and the iodolactone that would have been formed from 5b.
11. The use of other oxidizing agents invariably produced regioisomeric mixtures of olefinic products.
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