The first synthesis of (-)-pericosine E (6), a metabolite of the Periconia byssoides OUPS-N133 isolated originally from the sea hare Aplysia kurodai, has been achieved. Efficient and regioselective synthetic procedures for the synthesis of key intermediates, anti- and syn-epoxides 9 and 10, were developed using an anti-epoxidation of diene 12 with TFDO and a bromohydrination of 12 with NBS in CH(3)CN/H(2)O (2:3), respectively. In addition, comparison of the specific optical rotations between synthetic 6 and natural 6 elucidated that the naturally preferred enantiomer of pericosine E had the same absolute configuration as (-)-6 synthesized from chlorohydrin (-)-8 and anti-epoxide (+)-9.

Synthesis of Marine Natural Product (-)-Pericosine E. -The first synthesis of (-)-pericosine E is described. -(MIZUKI, K.; IWAHASHI, K.; MURATA, N.; IKEDA, M.; NAKAI, Y.; YONEYAMA, H.; HARUSAWA, S.; USAMI*, Y.; Org. Lett. 16 (2014) 14, 3760-3763, http://dx.