CSIRO Publishing blank image blank image blank image blank imageBooksblank image blank image blank image blank imageJournalsblank image blank image blank image blank imageAbout Usblank image blank image blank image blank imageShopping Cartblank image blank image blank image You are here: Journals > Australian Journal of Chemistry   
Australian Journal of Chemistry
Journal Banner
  An international journal for chemical science
 
blank image Search
 
blank image blank image
blank image
 
  Advanced Search
   

Journal Home
About the Journal
Editorial Board
Contacts
For Advertisers
Content
Online Early
Current Issue
Just Accepted
All Issues
Virtual Issues
Special Issues
Research Fronts
Sample Issue
Covers
For Authors
General Information
Notice to Authors
Submit Article
Open Access
For Referees
Referee Guidelines
Review Article
For Subscribers
Subscription Prices
Customer Service
Print Publication Dates

blue arrow e-Alerts
blank image
Subscribe to our Email Alert or RSS feeds for the latest journal papers.

red arrow Connect with us
blank image
facebook   youtube

Affiliated with RACI

Royal Australian Chemical Institute
Royal Australian
Chemical Institute


 

Article << Previous     |     Next >>   Contents Vol 34(9)

Studies on gibberellin synthesis. Assembly of an ethanophenanthrenoid lactone and conversion into a gibbane derivative

LN Mander and SG Pyne

Australian Journal of Chemistry 34(9) 1899 - 1911
Published: 1981

Abstract

Diazoketone (13), prepared by standard methods from 5-formyl-8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (7), was cyclized in trifluoroacetic acid to dienone (1) which under-went intramolecular 1,4-conjugate addition to afford the ethanophenanthrene derivative (15). Refunctionalization furnished dibenzoyloxy diacid (19) which cyclized in sulfuric acid specifically to the 8-carboxy-10,12-dibenzoyloxyperhydro-1H-2,10a-ethanophenanthrene-8,4b-carbolactone (2). Further refunctionalization to ketone (22), then formation of diazoketone (23) followed by photolysis in an aqueous medium, finally gave (1RS,4aRS,4bRS,7SR,8SR,9aSR,10SR,10aRS)-8-benzoyloxy-4a-hydroxy-1-methoxymethyloxymethylgibbane-1,10-dicarboxylic acid 1,4a-lactone (3) which may serve both as a model and intermediate for a radically new approach to the total synthesis of gibberellins.



Full text doi:10.1071/CH9811899

© CSIRO 1981

blank image >
 
PDF (728 KB) $25
 Export Citation
 Print
  


  
Subscriber Login
Username:
Password:  

    
Legal & Privacy | Contact Us | Help

CSIRO

© CSIRO 1996-2013