HETEROCYCLES

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

■ 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

Abstract

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.