Elucidation of the stereocontrol mechanisms of the chemical and biosynthetic intramolecular Diels–Alder cycloaddition for the formation of bioactive decalins-Reference-Cited by-同舟云学术

Elucidation of the stereocontrol mechanisms of the chemical and biosynthetic intramolecular Diels–Alder cycloaddition for the formation of bioactive decalins

Published:2023 Issue:40 Volume:13 Page:27828-27838
ISSN:2046-2069
Container-title:RSC Advances
language:en
Short-container-title:RSC Adv.

Author:

Kariya Takumi¹,Hasegawa Hayato²,Udagawa Taro³^ORCID,Inada Yusaku¹,Nishiyama Kyoko⁴,Tsuji Mieko¹^ORCID,Hirayama Tasuku¹^ORCID,Suzutani Tatsuo⁴,Kato Naoki⁵^ORCID,Nagano Shingo⁶⁷^ORCID,Nagasawa Hideko¹^ORCID

Affiliation:

1. Laboratory of Pharmaceutical and Medicinal Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu, 501-1196, Japan

2. Department of Engineering, Graduate School of Sustainability Science, Tottori University, 4-101 Koyama-cho Minami, Tottori 680-8552, Japan

3. Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan

4. Department of Microbiology, Fukushima Medical University, 1 Hikarigaoka, Fukushima 960-1295, Japan

5. Faculty of Agriculture, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan

6. Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-cho Minami, Tottori 680-8552, Japan

7. Center for Research on Green Sustainable Chemistry, Tottori University, 4-101 Koyama-cho Minami, Tottori 680-8552, Japan

Abstract

This study elucidates the role of the absolute configuration at the C-6 carbon of the substrate polyene in the stereocontrol of the IMDA reaction catalyzed by Fsa2 and Phm7, which construct different enantiomeric decalin skeletons.

Funder

Japan Society for the Promotion of Science

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/RA/D3RA04406H

Reference37 articles.

1. The Diels-Alder Reaction in Total Synthesis

2. Natural [4 + 2]-Cyclases

3. Biocatalytic Strategies towards [4+2] Cycloadditions

4. The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery

5. Chemistry and Biology of Biosynthetic Diels–Alder Reactions