A biomimetic total synthesis of (+)-intricarene

ORGN 577

Bencan Tang, bencantang@yahoo.com.cn and Gerald Pattenden. Department of Chemistry, The University of Nottingham, UK, Lab B46 School of Chemistry University Park, the University of Nottingham, Nottingham, NG7 2RD, United Kingdom
Intricarene and bielschowskysin are two structurally intriguing polycyclic diterpenes which have recently been isolated from the coral Pseudopterogorgia kallos by Rodriguez et al. Bielschowskysin has been shown to display specific in vivo cytotoxicity against cell lung and renal cancer in the NCI antitumor screen. We believe these two natural products are related as significantly rearranged furanocembrane natural products which we have their origins in the furanobutenolide structure known as bipinnatin J, found in gorgonian corals: P. bipinnata.

My poster described an asymmetric synthesis of the furanocembrane (–)-bipinnatin J and its transformation into (+)-intricarene through a transannular oxidopyrilium-alkene [5+2] cycloaddition.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007