Total Synthesis and Structural Reassignment of Aranorosinol A, Aranorosinol B, and EI-2128-1.


Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
20 03 2020
Historique:
pubmed: 23 2 2020
medline: 24 6 2021
entrez: 21 2 2020
Statut: ppublish

Résumé

Herein, we report a concise and collective total synthesis of three natural products aranorosinol A, aranorosinol B, and EI-2128-1 and also the known penicimutanolone. A unified strategy was conceived, which divergently accessed all four congeners within 9-11 steps (LLS) from a common intermediate. Bisoxirane-directed 1,2-addition was utilized as a key step to generate the desired configuration of the C

Identifiants

pubmed: 32077282
doi: 10.1021/acs.joc.0c00028
doi:

Substances chimiques

EI 2128-1 0
Epoxy Compounds 0
Fatty Acids, Unsaturated 0
Spiro Compounds 0
aranorosinol A 145147-04-2
aranorosinol B 145147-05-3

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

4335-4343

Auteurs

Haiyong Yu (H)

Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.

Yingyuan Tian (Y)

Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.

Yan Zong (Y)

Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.

Jianyu Zhang (J)

Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.

Tao Xu (T)

Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.
Laboratory for Marine Drugs and Bioproducts & Open Studio for Druggability Research of Marine Natural Products, Pilot National Laboratory for Marine Science and Technology, 1 Wenhai Road, Qingdao 266237, China.

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Classifications MeSH