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Asymmetric Synthesis of the Aromatic Fragment of Sespendole
Yoshiki Ono1, Atsuo Nakazaki1, Kaori Ueki1
1Graduate School of Bioagricultural Sciences , Nagoya University , Furo-cho, Chikusa , Nagoya 464-8601 , Japan.
Abstract:
Sespendole is an indole sesquiterpene alkaloid bearing two isoprenyl groups, one of which is highly oxidized. Herein, we disclose an eight-step synthesis of the aromatic fragment of sespendole in an optically pure form, starting from 4-bromo-2-fluoronitrobenzene. The key steps were a Claisen rearrangement at room temperature for introduction of the prenyl group and a coupling between the dianion generated from prenylated bromo-N-tosylanilide and a chiral epoxy aldehyde.
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