New Synthetic Route to Granulatimide and Its Structural Analogues

Takuji Yoshida; Masakazu Nishiyachi; Nobuyuki Nakashima; Masayuki Murase; Eiichi Kotani

doi:10.1248/cpb.50.872

Notes

New Synthetic Route to Granulatimide and Its Structural Analogues

Takuji Yoshida, Masakazu Nishiyachi, Nobuyuki Nakashima, Masayuki Murase, Eiichi Kotani

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Keywords: alkaloid, indole, maleimide, imidazole, Stille coupling reaction, synthesis

JOURNAL FREE ACCESS

2002 Volume 50 Issue 6 Pages 872-876

DOI https://doi.org/10.1248/cpb.50.872

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Abstract

The Stille coupling reaction of stannylindole 12 with 4-iodoimidazole 13 (or 24) in the presence of PdCl₂(PPh₃)₂ gave the corresponding indole–imidazole coupling product 14 (or 25), thereby affording a new synthetic approach to the alkaloid granulatimide (7), isolated from the Brazilian ascidian Didemnum granulatum, as well as its structural analogues, 10-methylgranulatimide (23), 17-methylgranulatimide (30), 10,17-dimethylgranulatimide (31).

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