Synthesis and determination of the absolute configuration of (−)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni

• I. Wayan Mudianta,
• Victoria L. Challinor,
• Anne E. Winters,
• Karen L. Cheney,
• James J. De Voss and
• Mary J. Garson

Beilstein J. Org. Chem. 2013, 9, 2925–2933, doi:10.3762/bjoc.9.329

• , Australia 10.3762/bjoc.9.329 Abstract A small sample of (−)-(5R,6Z)-dendrolasin-5-acetate, which was fully characterized by 2D NMR studies, was isolated from the nudibranch Hypselodoris jacksoni, along with the sesquiterpenes (+)-agassizin, (−)-furodysinin, (−)-euryfuran, (−)-dehydroherbadysidolide and

• obtained by preparative enantioselective HPLC. Keywords: enantioselective HPLC; E/Z-isomers; Hypselodoris; natural products; nudibranch; sesquiterpene; Introduction Marine organisms have been proven a prolific source of natural products that potentially can be used as lead compounds or which have

• (either directly or as a derivative) that have been approved for FDA use as a drug or are in clinical trials were first isolated from molluscs. For some of these bioactives, the actual biosynthetic source is a microorganism [6]. Within the Nudibranchia, the genus Hypselodoris is generally characterized by