Almost one year after my last lab work on this subject the centrepiece of my PhD thesis was published in Organic Letters. When I started my PhD in January 2015 at the University of Bonn in the research group of Prof. Dirk Menche my goal was to synthesize Archazolid F, a polyketide isolated in 2011. Now three years later I am happy to see the end on this journey as Organic Letters published the total synthesis of Archazolid F. Interestingly looking back to the initial synthesis plan a lot of key steps and connections have changed during this synthesis and a lot of effort was done in the macrocyclization of the macrolide.
Now the macrocyclization was done by ring-closing metathesis. It was quit a risky approach taking in aspect we talking about a polyene substrate and it also failed once. Compared to previous routes to archazolid A and B this was the first time a direct RCM was used. Although Dirk Trauner et al. could successfully establish a Relay RCM for the synthesis of archazolid B.
Furthermore the publication also featuring a bioinspired deconjugation reaction with DBU. It was very exiting and one of my best experiences in lab to evaluate this isomerization from archazolid B to archazolid F.