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Molecules 2005, 10(1), 312-316; doi:10.3390/10010312
Article

Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision

, ,  and *
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
* Author to whom correspondence should be addressed.
Received: 28 December 2004 / Revised: 24 January 2005 / Accepted: 24 January 2005 / Published: 31 January 2005
(This article belongs to the Special Issue Hypervalent Iodine)
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Abstract

Asymmetric synthesis of double bond isomers ( )-2 (∆15’,16’) and ( )-3 (∆14’,15’) ofthe structure (1) (∆16’,17’) proposed for pyrinodemin A, a cytotoxic bis-pyridine alkaloidwith a unique cis-cyclopent[c]isoxazolidine moiety from a marine sponge, has beenaccomplished. Pyrinodemin A was indicated to be a 1:1 racemic mixture of 2 fromcomparison of C18 and chiral HPLC analysis for pyrinodemin A and the syntheticcompounds as well as ESIMS data of oxidative degradation products of pyrinodemin A.
Keywords: Pyrinodemin A; Amphimedon sp.; asymmetric synthesis; structural revision Pyrinodemin A; Amphimedon sp.; asymmetric synthesis; structural revision
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Ishiyama, H.; Tsuda, M.; Endo, T.; Kobayashi, J. Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision. Molecules 2005, 10, 312-316.

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