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Molecules 2018, 23(9), 2351; https://doi.org/10.3390/molecules23092351

Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A1 via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions

1
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea
2
College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea
3
Center for Neuro-Medicine, Korea Institute of Science and Technology (KIST), Seoul 02792, Korea
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 1 September 2018 / Revised: 8 September 2018 / Accepted: 10 September 2018 / Published: 14 September 2018
(This article belongs to the Special Issue Stereogenic Centers)
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Abstract

The versatile synthesis of (−)-6-desmethyl-fluvirucinine A1 was accomplished at a 24% overall yield through a thirteen-step process from a known vinylpiperidine. The key part involved the elaboration of the distal stereocenters and a macrolactam skeleton via conformationally-induced diastereocontrol and the iterative aza-Claisen rearrangements of lactam precursors. View Full-Text
Keywords: fluvirucinine; aza-Claisen rearrangement; amidoalkylation fluvirucinine; aza-Claisen rearrangement; amidoalkylation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Moon, H.; Yoon, H.; Lim, C.; Jang, J.; Yi, J.-J.; Lee, J.K.; Lee, J.; Na, Y.; Son, W.S.; Kim, S.-H.; Suh, Y.-G. Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A1 via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions. Molecules 2018, 23, 2351.

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