Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

Tom D Ackrill, Hazel A Sparkes, Chris L Willis*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

15 Citations (Scopus)
274 Downloads (Pure)

Abstract

γ,δ-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the γ,δ-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.
Original languageEnglish
Pages (from-to)3884-3887
Number of pages4
JournalOrganic Letters
Volume17
Issue number15
DOIs
Publication statusPublished - 7 Aug 2015

Bibliographical note

Date of Acceptance: 24/07/2015

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