Enantioselective syntheses of (+)- and (-)-blastmycinolactol

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6621-6624

  Jacobi, Peter A ^a   Herradura, Prudencio ^a  

^a WESLEYAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CITRININ; MACROLIDE;

ARTICLE; CIS TRANS ISOMERISM; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030848424     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01533-5     Document Type: Article

References (46)

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2. Antimycin isolation: (a) Leben, C.; Keitt, G.W. Phytopath. 1948, 38, 899. (b) Watanabe, K.; Tanaka, T.; Fukuhara, K.; Miyairi, N.; Yonehara, H.; Umezawa, H. J. Antibiot. 1957, 10A, 39.
3. Blastmycinone isolation and structure: (a) Tener, G.M.; van Tamelen, E.E.; Strong, F.M. J. Am. Chem. Soc. 1953, 75, 3623.
4. (b) Yonehara, H.; Takeuchi, S. J. Antibiot. 1958, 11A, 122, 254.
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9. Blastmycinone synthesis: (a) de Azevedo, M.B.M.; Greene, A.E. J. Org. Chem. 1995, 60, 4940.
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14. (f) See also Ref. 2f and 3a-d.
15. Isolation: (a) Li. W.; Nihira, T.; Sakuda, S.; Nishida, T.; Yamada, Y. J. Ferment. Bioeng. 1992, 74, 214. Synthesis:
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28. (a) Stereochemical assignments were based upon literature precedent, spectral data, and by conversion to the target compounds (+)-1a (-)-1b.
29. Unpublished results, Dr. Wanjun Zheng, Wesleyan University.
30. (c) At T > 80 °C, mercaptans undergo competitive addition to the triple bond.
31. (d) BnOH is slowly converted to BnSH under the reaction conditions, but it is easily detectable when admixed.
32. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis; Second Edition, John Wiley & Sons, New York, 1991.
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36. (a) Volante, R.P. Tetrahedron Letters 1981, 22, 3119, and references cited therein. See also
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44. (g) Matsubara, S.; Takai, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1983, 56, 2029.
45. 23 = 16° (c = 1.60, MeOH).
46. Financial support of this work by NSF Grant No. CHE-9424476 is gratefully acknowledged.