Synthesis of (3R,5R)-harzialactone A and its (3R,5S)-isomer

• Gowravaram Sabitha,
• Rangavajjula Srinivas,
• Sukant K. Das and
• Jhillu S. Yadav

Beilstein J. Org. Chem. 2010, 6, No. 8, doi:10.3762/bjoc.6.8

• . Epoxide opening with thioacetal and diastereoselective reductions are used as key reactions. Keywords: dithiane; harzialactone A; hydroxyl directed reduction; stereoisomer; Introduction Marine microorganisms such as bacteria, fungi, and microalgae have proved to be a rich source of structurally novel

• successive protecting group transformations. 3 can be made by hydroxyl directed reduction of 4 which in turn could be prepared by epoxide 6 opening with dithiane 5. Results and Discussion The synthesis of natural (3R,5R)-1 was initiated from the known epoxide 6, which is commercially available. Treatment of