Document Detail


Total synthesis of gambierol: the generation of the A-C and F-H subunits by using a C-glycoside centered strategy.
MedLine Citation:
PMID:  16331718     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Gambierol, a representative of the marine ladder toxin family, consists of eight ether rings, 18 stereocenters, and two challenging pyranyl rings having methyl groups that are in a 1,3-diaxial orientation to one another. Herein we describe the generation of gambierol's A-C and F-H ring systems and demonstrate the versatility of the glycosyl anhydride, enol ether-olefin RCM strategy to fused polycyclic ethers. This work has both enabled us to generate sufficient quantities of the gambierol precursors and has enabled us to better understand the chemical transformations that were key to these efforts. Fundamental work included efforts to C-glycosides and C-ketosides, Claisen rearrangements, and enol ether-olefin RCM reactions.
Authors:
Utpal Majumder; Jason M Cox; Henry W B Johnson; Jon D Rainier
Related Documents :
20976328 - Ring-opening of cyclopropanes by "frustrated lewis pairs".
10990428 - Synthesis of the ring system of phomactin d using a suzuki macrocyclization.
17391048 - Dearomatizing anionic cyclization and novel skeletal rearrangement: high yield formatio...
17715968 - Synthesis of oxepane ring containing monocyclic, conformationally restricted bicyclic a...
24175318 - [(18)f]fluorination of o-carborane via nucleophilic substitution: towards a versatile p...
15979598 - N-alkyl derivatives of 2-amino-2-deoxy-d-glucose.
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  12     ISSN:  0947-6539     ISO Abbreviation:  Chemistry     Publication Date:  2006 Feb 
Date Detail:
Created Date:  2006-02-07     Completed Date:  2007-06-05     Revised Date:  2009-08-04    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  1736-46     Citation Subset:  IM    
Affiliation:
University of Utah, Department of Chemistry, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Ciguatera Poisoning
Ciguatoxins / chemical synthesis*
Cyclization
Epoxy Compounds / chemical synthesis
Ethers / chemistry
Ethers, Cyclic / chemical synthesis*
Glycosides / chemical synthesis*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Marine Toxins / chemical synthesis*
Polycyclic Compounds / chemical synthesis*,  chemistry
Grant Support
ID/Acronym/Agency:
GM56677/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Epoxy Compounds; 0/Ethers; 0/Ethers, Cyclic; 0/Glycosides; 0/Indicators and Reagents; 0/Marine Toxins; 0/Polycyclic Compounds; 0/gambierol; 11050-21-8/Ciguatoxins

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Dynamics in host-guest complexes of molecular tweezers and clips.
Next Document:  Total synthesis of gambierol: subunit coupling and completion.