Asymmetric synthesis of (+)-17-epi-methoxy-kauran-3-one through tandem oxidative polycyclization-pinacol process-Reference-Cited by-同舟云学术

Asymmetric synthesis of (+)-17-epi-methoxy-kauran-3-one through tandem oxidative polycyclization-pinacol process

Published:2016 Issue:28 Volume:14 Page:6744-6750
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Maertens Gaëtan¹²³⁴,Desjardins Samuel¹²³⁴,Canesi Sylvain¹²³⁴

Affiliation:

1. Laboratoire de Méthodologie et Synthèse de Produits Naturels

2. Université du Québec à Montréal

3. Montréal

4. Canada

Abstract

A synthesis of (+)-17-epi-methoxy-kauran-3-one, an O-methylated isomer of the natural diterpene 17-hydroxy-kauran-3-one, has been achieved. The strategy is based on a diastereoselective oxidative polycyclization-pinacol tandem process consisting in transforming a functionalized phenol into a compact and complex tetracycle.

Funder

Natural Sciences and Engineering Research Council of Canada

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2016/OB/C6OB01142J

Reference98 articles.

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3. Tonantzitlolone and other Diterpenes fromStillingia sanguinolenta