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

• Gowravaram Sabitha Rangavajjula Srinivas Sukant K. Das Jhillu S. Yadav Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India, Fax: +91-40-27160512 10.3762/bjoc.6.8 Abstract The total synthesis of (3R,5R)-harzialactone A (1) and its (3R,5S)-isomer (2) is described

• . 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

• and biologically active secondary metabolites [1]. (+)-Harzialactone A (1), a marine metabolite isolated from the culture broth of a strain of Trichoderma harzianum OUPS-N115 by Numata and co-workers, exhibited antitumor and cytotoxic activities against cultured P388 cells [2]. The absolute