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Molecules 2011, 16(6), 4850-4860; doi:10.3390/molecules16064850

Synthetic Studies on Bioactive Natural Polyketides: Intramolecular Nitrile Oxide-Olefin Cycloaddition Approach for Construction of a Macrolactone Skeleton of Macrosphelide B

1
College of Pharmacy, the Institute of Health Sciences, Gyeongsang National University, Jinju daero, Jinju, Gyeongnam, 660-751, Korea
2
College of Pharmacy, Seoul National University, Gwanak-ro 599, Gwanak-gu, Seoul 151-742, Korea
*
Author to whom correspondence should be addressed.
Received: 27 April 2011 / Revised: 26 May 2011 / Accepted: 7 June 2011 / Published: 10 June 2011
(This article belongs to the Special Issue Polyketide)
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Abstract

Studies on the synthesis of macrosphelide B via an intramolecular nitrile oxide-olefin cycloaddition (INOC) is described. In particular, an asymmetric INOC approach using phase transfer catalysts seems to be a potentially efficient and versatile procedure for the construction of the macrolactone skeleton of macrosphelide B in terms of facial selectivity. Our preliminary and unprecedented stereoselective procedure is anticipated to be usefully applied through further studies for the synthesis of the macrosphelide family.
Keywords: intramolecular nitrile oxide cycloaddition; macrosphelide; polyketide; total synthesis; phase transfer catalyst intramolecular nitrile oxide cycloaddition; macrosphelide; polyketide; total synthesis; phase transfer catalyst
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Paek, S.-M.; Suh, Y.-G. Synthetic Studies on Bioactive Natural Polyketides: Intramolecular Nitrile Oxide-Olefin Cycloaddition Approach for Construction of a Macrolactone Skeleton of Macrosphelide B. Molecules 2011, 16, 4850-4860.

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