Biomimetic Total Synthesis of Santalin Y

Sebastian Strych; Guillaume Journot; Ryan P. Pemberton; Selina C. Wang; Dean J. Tantillo; Dirk Trauner

doi:10.1002/anie.201411350

Biomimetic Total Synthesis of Santalin Y

Sebastian Strych, Guillaume Journot, Ryan P. Pemberton, Selina C. Wang, Dean J. Tantillo, Dirk Trauner

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A biomimetic total synthesis of santalin Y, a structurally complex but racemic natural product, is described. The key step is proposed to be a (3+2) cycloaddition of a benzylstyrene to a "vinylogous oxidopyrylium", which is followed by an intramolecular Friedel-Crafts reaction. This cascade generates the unique oxafenestrane framework of the target molecule and sets its five stereocenters in one operation. Our work provides rapid access to santalin Y and clarifies its biosynthetic relationship with other colorants isolated from red sandalwood.

Original language	English (US)
Pages (from-to)	5079-5083
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	17
DOIs	https://doi.org/10.1002/anie.201411350
State	Published - Apr 20 2015

Keywords

biomimetic synthesis
dipolar cycloaddition
polyphenols
racemic natural products
total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201411350

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AU - Strych, Sebastian

AU - Journot, Guillaume

AU - Pemberton, Ryan P.

AU - Wang, Selina C.

AU - Tantillo, Dean J.

AU - Trauner, Dirk

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Biomimetic Total Synthesis of Santalin Y

Abstract

Keywords

ASJC Scopus subject areas

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