Asymmetric Synthesis of the Aromatic Fragment of Sespendole

Yoshiki Ono, Atsuo Nakazaki, Kaori Ueki, Keiko Higuchi, Uraiwan Sriphana, Masaatsu Adachi, Toshio Nishikawa

Research output: Contribution to journalArticlepeer-review

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. ©

Original languageEnglish
Pages (from-to)9750-9757
Number of pages8
JournalJournal of Organic Chemistry
Volume84
Issue number15
DOIs
Publication statusPublished - 2019 Aug 2
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Asymmetric Synthesis of the Aromatic Fragment of Sespendole'. Together they form a unique fingerprint.

Cite this