Next Article in Journal
Novel Enzyme Actions for Sulphated Galactofucan Depolymerisation and a New Engineering Strategy for Molecular Stabilisation of Fucoidan Degrading Enzymes
Previous Article in Journal
In Vitro Anticancer and Proapoptotic Activities of Steroidal Glycosides from the Starfish Anthenea aspera
Previous Article in Special Issue
Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry
Article Menu
Issue 11 (November) cover image

Export Article

Open AccessArticle
Mar. Drugs 2018, 16(11), 421; https://doi.org/10.3390/md16110421

Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues

Department of Organic Chemistry, Faculty of Science, Campus Miguel Delibes, 47011 Valladolid, Spain
*
Author to whom correspondence should be addressed.
Received: 9 September 2018 / Revised: 19 October 2018 / Accepted: 25 October 2018 / Published: 1 November 2018
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
Full-Text   |   PDF [2071 KB, uploaded 1 November 2018]   |  

Abstract

Tetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid-mediated cyclization of silylated alkenols is described. p-TsOH has shown to be an efficient reagent to yield highly substituted tetrahydropyrans. Moreover, excellent diastereoselectivities are obtained both for unsubstituted and alkylsubstituted vinylsilyl alcohols. The methodology herein developed may potentially be applied to the synthesis of marine drugs derivatives. View Full-Text
Keywords: tetrahydropyrans; acid mediated cyclization; stereoselective; marine drugs analogues tetrahydropyrans; acid mediated cyclization; stereoselective; marine drugs analogues
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Díez-Poza, C.; Val, P.; Pulido, F.J.; Barbero, A. Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues. Mar. Drugs 2018, 16, 421.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top