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Synlett 1999; 1999(5): 541-544
DOI: 10.1055/s-1999-2689
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Synthesis of the B,C,D,E,F-Ring Fragment of Pinnatoxins

Tetsuya Sugimoto* , Jun Ishihara, Akio Murai
  • *Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, 060-0810, Japan; Fax 81-11-7 06-27 14; E-mail: amurai@sci.hokudai.ac.jp
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Publication Date:
31 December 1999 (online)

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Construction of the B,C,D,E,F-ring of pinnatoxins is disclosed. Julia coupling reaction between the E,F-ring fragment (C26-C31) as the sulfone and the B,C,D-ring fragment (C10-C25) as the aldehyde proceeded smoothly to afford the B,C,D,E,F-ring system via acetalization.

pinnatoxin - dispiroacetal - trioxadispiro[5.1.5.2]pentadecane dioxabicyclo[3.2.1]octane