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

doi:10.3390/10010312

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

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

Haruaki Ishiyama, Masashi Tsuda, Tadashi Endo and Jun’ichi Kobayashi*

Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan

* Author to whom correspondence should be addressed.

Received: 28 December 2004; in revised form: 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 C₁₈and 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

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MDPI and ACS Style

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.

AMA Style

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(1):312-316.

Chicago/Turabian Style

Ishiyama, Haruaki; Tsuda, Masashi; Endo, Tadashi; Kobayashi, Jun’ichi. 2005. "Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision." Molecules 10, no. 1: 312-316.

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