Tetrahedron p. 8999 - 9010 (1998)
Update date:2022-08-16
Topics:
Iwao, Masatomo
Motoi, Osamu
Fukuda, Tsutomu
Ishibashi, Fumito
A new entry into pyrroloiminoquinone marine alkaloids, makaluvamines, has been developed. The key 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline intermediates 11 and 18 were prepared by aryne-mediated cyclization of the 4- chloro-6-methoxytryptamine derivatives 10 and 17, respectively. The requisite substituents at the indole 4- and 3-positions of 10 and 17 were efficiently assembled by sequential use of directed lithiation of 1-triisopropylsilyl-6- methoxygramine (6) and fluoride ion-induced elimination-addition of the methiodide of 4-chloro-l-triisopropylsilyl-6-methoxygramine (7) as key reactions.
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