Toward the Synthesis of Paspaline-Type Indole-Terpenes: Stereoselective Construction of Core Scaffold with Contiguous Asymmetric Quaternary Carbon Centers

Ichiro Hayakawa, Naochika Matsumaru, Akira Sakakura

Research output: Contribution to journalArticlepeer-review

Abstract

The core scaffold of paspaline-type indole-terpenes was synthesized by using the House-Meinwald rearrangement as a key step. Rearrangement of the epoxide methyl group in the precursor with methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) as a Lewis acid proceeded smoothly to construct contiguous asymmetric quaternary carbon centers by a 1,2-chirality transfer.

Original languageEnglish
Pages (from-to)9802-9810
Number of pages9
JournalJournal of Organic Chemistry
Volume86
Issue number14
DOIs
Publication statusPublished - Jul 16 2021

ASJC Scopus subject areas

  • Organic Chemistry

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