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Paper | Regular issue | Vol 91, No. 5, 2015, pp.970-988
Published online, 9th April, 2015
DOI: 10.3987/COM-15-13195
Synthesis and Synthesis-Based Structural Elucidation of ()-Macrosphelides J and K

Hongchan An, Seung-Hee Kim, Heegyu Kim, Kyeojin Kim, Jaehoon Sim, Jaebong Jang, Seung-Mann Paek, Young-Ger Suh, and Hwayoung Yun*

*College of Pharmacy, Pusan National University, 63 Beon-gil 2, Busandaehag-ro, Geumjeong-gu, Busan 609-735, Korea


The structures of (‒)-macrosphelides J and K have been elucidated via asymmetric total syntheses. Key points of the structure elucidation include an initial prediction of the stereochemistries of (‒)-macrosphelides J and K based on the structural relationship of the macrosphelides and molecular modeling of macrosphelide B. Our synthetic approach features an isoxazoline-based route involving a diastereoselective olefin-nitrile oxide cycloaddition, an intricate reductive N-O bond cleavage of an isoxazoline and O-alkylation of the labile β-hydroxy ketone intermediate.