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. 2018 Sep 14;23(9):2351.
doi: 10.3390/molecules23092351.

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

Hyunyoung Moon  1   2 , Hojong Yoon  3 , Changjin Lim  4   5 , Jaebong Jang  6 , Jong-Jae Yi  7 , Jae Kyun Lee  8 , Jeeyeon Lee  9 , Younghwa Na  10 , Woo Sung Son  11 , Seok-Ho Kim  12 , Young-Ger Suh  13   14
Affiliations

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

Hyunyoung Moon et al. Molecules. .

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.

Keywords: amidoalkylation; aza-Claisen rearrangement; fluvirucinine.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of fluvirucins.
Figure 2
Figure 2
6-Desmethyl-fluvirucinine A1 (11) and the carbohydrate part (12) of 6-desmethyl-N-methylfluvirucin A1 (8).
Scheme 1
Scheme 1
Retrosynthetic analysis for synthesis of 13 as an antipode of 11.
Scheme 2
Scheme 2
Preparation and diastereoselective amidoalkylation of 16.
Scheme 3
Scheme 3
Synthesis of macrolactam 26.
Figure 3
Figure 3
X-ray crystallographic structure of 32. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii; black = carbon, red = oxygen, blue = nitrogen, and yellow = silicon.
Scheme 4
Scheme 4
Completion of the (−)-6-demethyl-fluvirucinine A1 (13) synthesis.
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