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Note | Regular issue | Vol 63, No. 4, 2004, pp.885-893
Published online, 6th February, 2004
DOI: 10.3987/COM-03-10000
Synthesis of the ABCD Ring System of Azaspiracid, a Marine Poison from Mytilus edulis

Yuichi Ishikawa and Shigeru Nishiyama*

*Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan


Synthesis of the ABCD ring system of azaspiracid (1) was accomplished. The bridge system between the B and C rings using a sulfur atom, supported the spiroacetal-construction at the C13 position in the natural form. The stereochemistry was confirmed by the NOE experiments, along with conversion under acidic conditions into the unnatural derivative (12).