Total Synthesis of (+)-Maritimol

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.

Publication History

Article published online:
13 February 2023