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

Hyunyoung Moon, Hojong Yoon, Changjin Lim, Jaebong Jang, Jong-Jae Yi, Jae Kyun Lee, Jeeyeon Lee, Younghwa Na, Woo Sung Son, Seok-Ho Kim and Young-Ger Suh

Molecules, 23(9), 2351, doi:10.3390/molecules23092351

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

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