Abstract
A detailed investigation of ring B contraction has been carried out with several derivatives containing the ent-3β,20-epoxy-3,16α-dimethoxy-17-norkaurane skeleton (1). The 19,6β-lactone 7α-methanesulphonate (3) on treatment with base and subsequent methylation gave the gibberellane aldehyde (8) and the epimeric norkaurane derivative (9). The 6β-hydroxy-7α-methanesulphonate (4) on similar treatment gave a similar result. The 19,6α-lactone 7α-methanesulphonate (6) on treatment with potassium hydroxide in t-butyl alcohol–water and subsequent methylation afforded only the desired product (8), in almost quantitative yield. The ring B contraction reaction did not proceed with the 6β-methanesulphonate 7α-acetate (7). The results are rationalised in terms of stereochemical considerations.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
