RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
Synfacts 2023; 19(03): 0219
DOI: 10.1055/s-0042-1753351
DOI: 10.1055/s-0042-1753351
Synthesis of Natural Products
Total Synthesis of (+)-Maritimol
Toró A,
Nowak P,
Deslongchamps P.
*
Université de Sherbrooke, Quebec, Canada
Transannular Diels–Alder Entry into Stemodanes: First Asymmetric Total Synthesis of (+)-Maritimol.
J. Am. Chem. Soc. 2000;
122: 4526-4527
DOI: 10.1021/ja000728f
Transannular Diels–Alder Entry into Stemodanes: First Asymmetric Total Synthesis of (+)-Maritimol.
J. Am. Chem. Soc. 2000;
122: 4526-4527
DOI: 10.1021/ja000728f
Key words
(+)-maritimol - diterpenoid - Takai reaction - Stille coupling - Appel reaction - Dess–Martin oxidation - Diels–Alder reaction - Peterson olefination - Thorpe–Ziegler reaction
Significance
In 2000, Deslongchamp and co-workers reported the first asymmetric total synthesis of the diterpenoid (+)-maritimol. Key to their approach is a transannular Diels–Alder (TADA) reaction.
#
Comment
Stille coupling of vinyl iodide E and stannane C, followed by Appel reaction gave access to acyclic tetraene G. Base-mediated macrocyclization, deprotection and oxidation furnished aldehyde I, which undergoes the desired TADA reaction and decarboxylation upon heating.
#
#
Publikationsverlauf
Artikel online veröffentlicht:
13. Februar 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany