(Chemical Equation Presented) Starting from diethyl (R)-malate, synthesis of the lower-half segment of (+)-tubelactomicin A, a 16-membered macrolide antibiotic, has been achieved. The synthesis involved the highly endo- and π-facial selective intramolecular Diels-Alder reaction achieved using a trisubstituted methacrolein derivative tethering a 10-carbon dienyne unit at the β-carbon, which in turn was prepared from a known allylated malic acid derivative.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry