Total Synthesis of (+)-Superstolide A
Mariola Tortosa
Neal A. Yakelis
William R. Roush
10.1021/jo801794s.s001
https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_Superstolide_A/2891320
A convergent and highly stereocontrolled total synthesis of the cytotoxic macrolide (+)-superstolide A is described. Key features of this synthesis include the use of bimetallic linchpin <b>36b</b> for uniting the C(1)−C(15) (<b>43</b>) and the C(20)−C(27) (<b>38</b>) fragments of the natural product, a late-stage Suzuki macrocyclization of <b>49</b>, and a highly diastereoselective transannular Diels−Alder reaction of macrocyclic octaene <b>4</b>. In contrast, the intramolecular Diels−Alder reaction of pentaenal <b>5</b> provided the desired cycloadduct with lower stereoselectivity (6:1:1).
2008-12-19 00:00:00
diastereoselective
intramolecular
macrocyclic octaene 4.
macrocyclization
Suzuki
Diel
contrast
synthesis
bimetallic linchpin 36 b
fragment
stereocontrolled
Superstolide
transannular
stereoselectivity
Key features
convergent
cycloadduct
cytotoxic
macrolide
Total Synthesis
pentaenal 5
superstolide