Convergent total synthesis of (+)-muricatetrocin B, a
tetrahydrofuran-containing
acetogenin with potent and selective cytotoxicity against the HT-29
human colon adenocarcinoma cell line, was achieved in 13 steps. Our
synthesis is highlighted by a late-stage sequential olefin cross-metathesis/Hartung–Mukaiyama
cyclization for convergent assembly of the 2,5-trans-substituted tetrahydrofuran ring.
A seven-step synthesis of (−)-atorvastatin calcium, an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase, has been developed. The key transformations of the present synthesis are a tandem olefin cross-metathesis/hemiacetalization/intramolecular oxa-Michael addition and a subsequent regioselective Baeyer–Villiger oxidation for the stereocontrolled construction of the syn-3,5-dihydroxy carboxylic acid substructure.
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