Progress toward the total synthesis of N-methylwelwitindolinone C isothiocyanate

ORGN 413

Damian A. Allen, dallen@chem.ucla.edu and Michael E. Jung. Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569
N-Methylwelwitindolinone C Isothiocyanate (1) was isolated in 1994 from the blue green algae H. welwitschii and has been shown to reverse P-glycoprotein mediated multi-drug resistance and to induce microtubule depolymerization. Compound 1 is also a unique bicyclo [4.3.1] decanone composed of an oxindole and a densely functionalized cyclohexanone linked through a 7-membered ring. A highly regio and stereoselective Diels Alder reaction was used to construct a highly elaborated AD ring system. These results, along with progress toward the closure of the BC ring, will be presented.