Brief syntheses of (+)-blastmycinone and related γ-lactones from an asymmetrically dihydroxylated carboxylic ester

Tetrahedron

Volumn 54, Issue 38, 1998, Pages 11461-11470

  Berkenbusch, Thilo ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Asymmetric Synthesis; Hydroxylation; Lactones; Osymlation; Silicon and compounds

Indexed keywords

BLASTMYCINONE; BUTENOLIDE; CITRININ; ESTER; FUNGICIDE; GAMMA LACTONE DERIVATIVE; INSECTICIDE; LACTONE; SILICON; SILYLLACTONE; UNCLASSIFIED DRUG;

ALKYLATION; ANTIFUNGAL ACTIVITY; ARTICLE; CHIRALITY; DEHYDRATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROXYLATION; OXIDATION; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0032541595     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00687-5     Document Type: Article

References (44)

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22. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
23. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
24. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
25. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
26. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
27. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
28. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
29. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
30. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
31. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
32. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
33. [11] Further syntheses, for instance of (-)-3, include Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994, 50, 8337-8346. Mikami K, Terada M, Nakai T. J. Chem. Soc., Chem. Commun. 1993, 343-345. Nishide K, Aramata A, Kamanaka T, Node M. Heterocycles 1993, 36, 2237-2240. Inghardt T, Frejd T. Tetrahedron 1991, 47, 6483-6492. Mulzer J, Schulze T, Strecker A, Denzer W. J. Org. Chem. 1988, 53, 4098-4103. Bernardi A, Beretta MG, Colombo L, Gennari C, Poli G, Scolastico C. J. Org. Chem. 1985, 50, 4442-4447. Uenishi J, Tomozane H, Yamoto M. J. Chem. Soc., Chem. Commun. 1985, 717-719. Sayo N, Nakai E, Nakai T. Chem. Lett. 1985, 1723-1724. Uchiyama H, Kobayashi Y, Sato F. Chem. Lett. 1985, 467-470. Gennari C, Bernardi A, Cardani S, Scolastico C. Tetrahedron 1984, 40, 4059-4065. Fujisawa T, Kohama H, Tajima K, Sato T. Tetrahedron Lett. 1984, 25, 5155-5156. Aburaki S, Konishi N, Kinoshita M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259. Cf. also ref. 8-10, 12, 13.
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42. [18] Procedure: Fleming I, Henning R, Parker DC, Plant HE, Sanderson, PEJ. J. Chem. Soc. Perkin Trans. 1 1995, 317-337.
43. 3H (Renders F, Hoppe D. Synthesis 1992, 865-870) gave closely related trans,trans-γ-lactones.
44. 3H (Renders F, Hoppe D. Synthesis 1992, 865-870) gave closely related trans,trans-γ-lactones.