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

ABSTRACT: The versatile synthesis of (-)-6-desmethyl-fluvirucinine A? 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.

SUBMITTER: Moon H

PROVIDER: S-EPMC6225218 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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

Moon Hyunyoung H Yoon Hojong H Lim Changjin C Jang Jaebong J Yi Jong-Jae JJ Lee Jae Kyun JK Lee Jeeyeon J Na Younghwa Y Son Woo Sung WS Kim Seok-Ho SH Suh Young-Ger YG

Molecules (Basel, Switzerland) 20180914 9

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. ...[more]

PMID: 30223428

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