Next Article in Journal
Novel Sulfamide-Containing Compounds as Selective Carbonic Anhydrase I Inhibitors
Next Article in Special Issue
Recent Advances in Substrate-Controlled Asymmetric Cyclization for Natural Product Synthesis
Previous Article in Journal
Improved Method for Reliable HMW-GS Identification by RP-HPLC and SDS-PAGE in Common Wheat Cultivars
Previous Article in Special Issue
Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes
Article Menu
Issue 7 (July) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(7), 1041; doi:10.3390/molecules22071041

General Methodologies Toward cis-Fused Quinone Sesquiterpenoids. Enantiospecific Synthesis of the epi-Ilimaquinone Core Featuring Sc-Catalyzed Ring Expansion

1
Eugene F. Merkert Chemistry Center, Boston College, 2609 Beacon Street, Chestnut Hill, MA 02467, USA
2
Ahmanson Science Center, California Lutheran University, 60 West Olsen Rd., Thousand Oaks, CA 91360, USA
*
Author to whom correspondence should be addressed.
Received: 1 June 2017 / Revised: 21 June 2017 / Accepted: 21 June 2017 / Published: 24 June 2017
(This article belongs to the Special Issue Asymmetric Synthesis 2017)
View Full-Text   |   Download PDF [2921 KB, uploaded 24 June 2017]   |  

Abstract

A stereocontrolled approach to the cis-decalin framework of clerodane diterpenes and biologically active quinone sesquiterpenes is reported. Starting from an inexpensive optically pure tetrahydroindanone, Birch reductive alkylation builds two new contiguous chiral centers—one of which is quaternary and all-carbon-substituted. Also featured is a highly regioselective diazoalkane—carbonyl homologation reaction to prepare the 6,6-bicyclic skeleton. Therein, the utility of Sc(OTf)3 as a mild catalyst for formal 1C insertion in complex settings is demonstrated. View Full-Text
Keywords: quinone natural products; quaternary carbon synthesis; cis-decalin; scandium triflate; catalytic ring expansion; homologation; (trimethylsilyl)diazomethane; hexahydroindanones; 5-epi-ilimaquinone; 5-epi-isospongiaquinone quinone natural products; quaternary carbon synthesis; cis-decalin; scandium triflate; catalytic ring expansion; homologation; (trimethylsilyl)diazomethane; hexahydroindanones; 5-epi-ilimaquinone; 5-epi-isospongiaquinone
Figures

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 alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Kaplan, H.Z.; Rendina, V.L.; Kingsbury, J.S. General Methodologies Toward cis-Fused Quinone Sesquiterpenoids. Enantiospecific Synthesis of the epi-Ilimaquinone Core Featuring Sc-Catalyzed Ring Expansion. Molecules 2017, 22, 1041.

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]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top