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Paper | Special issue | Vol 93, No. 1, 2016, pp.259-294
Published online, 30th November, 2015
DOI: 10.3987/COM-15-S(T)40
Simple Synthetic Method for 1,2,3,3a,8,8a-Hehahydropyrrolo[2,3-b]indoles Having a Halogen or an Oxygen Functional Group at the 3a-Position

Takako Iwaki, Yoshikazu Fukui, Masaki Okigawa, Fumio Yamada, Yoshiyuki Nagahama, Sachiko Ogasawara, Satomi Tanaka, Shiho Funaki, and Masanori Somei*

*Noto Marine Laboratory, Institute of Nature and Environmental Technology, Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, 56-7 Matsuhidai, Matsudo-shi, Chiba 270-2214, Japan


1-Methoxy-Nb-methoxycarbonyltryptamine derivatives are successfully converted by either halogenating reagents or iodine/morpholine to 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indoles having a halogen or an oxygen functional group at the 3a-position. Synthesis of the corresponding methyl 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylates is also reported.