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; Young Ger Suh

doi:10.3390/molecules23092351

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^*
, Young Ger Suh

^*Corresponding author for this work

Department of Pharmacy

CHA University
Seoul National University
Korea Institute of Science and Technology

Research output: Contribution to journal › Journal article › peer-review

3 Scopus citations

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.

Original language	English
Article number	2351
Journal	Molecules
Volume	23
Issue number	9
DOIs	https://doi.org/10.3390/molecules23092351
State	Published - 2018.09.14

Keywords

Amidoalkylation
Aza-Claisen rearrangement
Fluvirucinine

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10.3390/molecules23092351

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title = "Asymmetric synthesis of (−)-6-desmethyl-fluvirucinine A1 via conformationally-controlled diastereoselective lactam-ring expansions",

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",

author = "Hyunyoung Moon and Hojong Yoon and Changjin Lim and Jaebong Jang and Yi, \{Jong Jae\} and Lee, \{Jae Kyun\} and Jeeyeon Lee and Younghwa Na and Son, \{Woo Sung\} and Kim, \{Seok Ho\} and Suh, \{Young Ger\}",

year = "2018",

month = sep,

day = "14",

doi = "10.3390/molecules23092351",

language = "English",

volume = "23",

journal = "Molecules",

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T1 - Asymmetric synthesis of (−)-6-desmethyl-fluvirucinine A1 via conformationally-controlled diastereoselective lactam-ring expansions

AU - Moon, Hyunyoung

AU - Yoon, Hojong

AU - Lim, Changjin

AU - Jang, Jaebong

AU - Yi, Jong Jae

AU - Lee, Jae Kyun

AU - Lee, Jeeyeon

AU - Na, Younghwa

AU - Son, Woo Sung

AU - Kim, Seok Ho

AU - Suh, Young Ger

PY - 2018/9/14

Y1 - 2018/9/14

N2 - 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.

AB - 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.

KW - Amidoalkylation

KW - Aza-Claisen rearrangement

KW - Fluvirucinine

UR - https://www.scopus.com/pages/publications/85053621093

U2 - 10.3390/molecules23092351

DO - 10.3390/molecules23092351

M3 - Journal article

C2 - 30223428

AN - SCOPUS:85053621093

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

IS - 9

M1 - 2351

ER -

Asymmetric synthesis of (−)-6-desmethyl-fluvirucinine A₁ via conformationally-controlled diastereoselective lactam-ring expansions

Abstract

Keywords

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