Total Syntheses of β‐ and γ‐Naphthocyclinones
Abstract: After half a century from their isolation in 1974, we report the first total syntheses of β‐ and γ‐naphthocyclinones, two dimeric pyranonaphthoquinones featuring an unusual bicyclo[3.2.1]‐octadienone core. The syntheses were achieved with full stereochemical control and functional group management, relying on 1) enantioselective construction of the bicyclic core by Rh‐catalyzed enantioselective 1,4‐addition followed by thiolate‐mediated reductive cyclization, and 2) judicious design of a common chiral, non‐racemic monomer unit that is capable of divergence into the donor and acceptor units, and reunion to construct the bicyclo[3.2.1]octadienone core.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
Total Syntheses of β‐ and γ‐Naphthocyclinones ; day:11 ; month:11 ; year:2024 ; extent:8
Angewandte Chemie ; (11.11.2024) (gesamt 8)
- Creator
-
Ando, Yoshio
Hoshino, Taiju
Tanaka, Nozomi
Maturi, Mark M.
Nakazawa, Yusuke
Fukazawa, Takumi
Ohmori, Ken
Suzuki, Keisuke
- DOI
-
10.1002/ange.202415108
- URN
-
urn:nbn:de:101:1-2411121329213.396799947193
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
15.08.2025, 7:32 AM CEST
Data provider
This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Ando, Yoshio
- Hoshino, Taiju
- Tanaka, Nozomi
- Maturi, Mark M.
- Nakazawa, Yusuke
- Fukazawa, Takumi
- Ohmori, Ken
- Suzuki, Keisuke
Other Objects (12)
Total syntheses of Ganoderma meroterpenoids
Total syntheses of Leupyrrin A1 and B1
Total syntheses of shizukaols A and E
Total Syntheses of β‐ and γ‐Naphthocyclinones
Organocatalytic Total Syntheses of (+)- and (–)-Trigonoliimine A
Total Syntheses of Benzastatin E and Virantmycin
Total Syntheses of Hosieines A–C
Total syntheses of Tetrodotoxin and 9-epiTetrodotoxin
Total Syntheses of (+)-Norcembrene 5 and (+)-Pepluanol A
Electrochemically Enabled Total Syntheses of Natural Products
Total Syntheses of Ampelopsin D, Pallidol, and Quadrangularin A
A review of the total syntheses of triptolide
Total syntheses of Ganoderma meroterpenoids
Total syntheses of Leupyrrin A1 and B1
Total syntheses of shizukaols A and E
Total Syntheses of β‐ and γ‐Naphthocyclinones
Organocatalytic Total Syntheses of (+)- and (–)-Trigonoliimine A
Total Syntheses of Benzastatin E and Virantmycin
Total Syntheses of Hosieines A–C
Total syntheses of Tetrodotoxin and 9-epiTetrodotoxin
Total Syntheses of (+)-Norcembrene 5 and (+)-Pepluanol A
Electrochemically Enabled Total Syntheses of Natural Products
Total Syntheses of Ampelopsin D, Pallidol, and Quadrangularin A
A review of the total syntheses of triptolide
Total syntheses of Ganoderma meroterpenoids
Total syntheses of Leupyrrin A1 and B1
Total syntheses of shizukaols A and E
Total Syntheses of β‐ and γ‐Naphthocyclinones
Organocatalytic Total Syntheses of (+)- and (–)-Trigonoliimine A
Total Syntheses of Benzastatin E and Virantmycin
Total Syntheses of Hosieines A–C
Total syntheses of Tetrodotoxin and 9-epiTetrodotoxin
Total Syntheses of (+)-Norcembrene 5 and (+)-Pepluanol A
Electrochemically Enabled Total Syntheses of Natural Products
Total Syntheses of Ampelopsin D, Pallidol, and Quadrangularin A