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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Concise syntheses of (+)-macrosphelides A and B: studies on the macro-ring closure strategy
Seung-Mann Paek1, Hwayoung Yun, Nam-Jung Kim
1College of Pharmacy, Seoul National University, Gwanak-ro 599, Gwanak-gu, Seoul 151-742, Korea.
Abstract:
Highly concise syntheses of (+)-macrosphelides A and B were accomplished in this study. The key feature of our synthetic route involved the direct three-carbon homologation of the readily available Weinreb amide 6 by the addition of a trans-vinylogous ester anion equivalent and facile construction of the 16-membered macrolide skeleton of macrosphelides via an intramolecular nitrile oxide-olefin cycloaddition. The syntheses of macrosphelides A and B were completed with a 30 and 20% overall yield, respectively. This paper describes the details of our syntheses.
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