Concise syntheses of (+)-macrosphelides A and B: studies on the macro-ring closure strategy.
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.
Paek
Seung-Mann
SM
College of Pharmacy, Seoul National University, Gwanak-ro 599, Gwanak-gu, Seoul 151-742, Korea.
Yun
Hwayoung
H
Kim
Nam-Jung
NJ
Jung
Jong-Wha
JW
Chang
Dong-Jo
DJ
Lee
Sujin
S
Yoo
Jakyung
J
Park
Hyun-Ju
HJ
Suh
Young-Ger
YG
D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D009569:Nitric Oxide / Q000737:chemistry
D006571:Heterocyclic Compounds; C097798:macrosphelide A; C097799:macrosphelide B; D009569:Nitric Oxide