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Communication | Regular issue | Vol 43, No. 1, 1996, pp.1-6
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7243
Synthesis of Optically Active O,O,O-Trimethylkorupensamines A and B

A.V. Rama Rao,* Mukund K. Gurjar, D. Venkata Ramana, and Abhay K. Chheda

*Indian Institute of Chemical Technology, Hyderabad 500 007, India

Abstract

Hydrolysis of benzofuran derivative (10) with concomitant aromatisation produced the biaryl system (11). Subsequent Sharpless asymmetric epoxidation of the cinnamyl alcohol (13) gave atropisomers (14) and (15) conveniently separated by chromatography. Independent derivatisation of naphthylisoquinoline ring with 14 and 15 furnished korupensamine analogues (18) and (19). Comparison of CD spectra with those of natural products assigned the stereostructures of 18 and 19.