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Literature DB >> 23659351

Synthesis of the C4-epi-lomaiviticin B core reveals subtle stereoelectronic effects.

Abstract

An efficient synthesis of the C4-epi-lomaiviticin B core is reported. The synthesis features a diastereoselective anionic formal furan Diels-Alder reaction and a stereoselective oxidative enolate dimerization. During the investigation, subtle yet critical stereoelectronic effects imparted by the C4-stereocenter were observed.

Entities: Chemical

Mesh：

Substances：
Fluorenes
lomaiviticin B

Year: 2013 PMID： 23659351 DOI： 10.1021/ol400832r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

6 in total

1. Discovery of the lomaiviticin biosynthetic gene cluster in Salinispora pacifica.

Authors: Jeffrey E Janso; Brad A Haltli; Alessandra S Eustáquio; Kerry Kulowski; Abraham J Waldman; Li Zha; Hitomi Nakamura; Valerie S Bernan; Haiyin He; Guy T Carter; Frank E Koehn; Emily P Balskus
Journal: Tetrahedron Date: 2014-07-08 Impact factor: 2.457

Synthesis of the C4-epi-lomaiviticin B core reveals subtle stereoelectronic effects.

1. Discovery of the lomaiviticin biosynthetic gene cluster in Salinispora pacifica.

Review 2. Rearrangements of organic peroxides and related processes.

3. Multigram Synthesis of 1-O-Acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-L-pyrrolosamine.

4. Stereocontrolled Synthesis of the Fully Glycosylated Monomeric Unit of Lomaiviticin A.

5. Structure Revision of the Lomaiviticins.

6. Synthesis of the bis(cyclohexenone) core of (-)-lomaiviticin A.