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Communication | Regular issue | Vol 32, No. 5, 1991, pp.873-878
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5732
Ergot Alkaloids: The First and Five Step Total Syntheses of (—)- and (+)-6,7-Secoagroclavines, and the Syntheses of (—)- and (+)-6-Nor-6-propyl-6,7-secoagroclavines ((—)- and (+)-KSU 1415)

Kyoko Nakagawa and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

Simple synthetic method for optically active 4,5-trans-((—)- and (+)-6) and 4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz[cd]indoles ((—)- and (+)-7) was developed. Using these chiral common synthetic intermediates, the first total syntheses of (—)- and (+)-6,7-secoagroclavines were achieved in only five steps. Preparations of (—)- and (+)-6-nor-6-propyl-6,7-secoagroclavines ((—)- and (+)-KSU 1415) are also described.