Abstract
The synthesis of the retinoid skeleton has been exhaustively explored using the Stille coupling for the formation of the side-chain single bonds. On employing the experimental catalytic conditions developed by Farina [Pd 2(dba) 3, AsPh 3, NMP] we have modified the electronic and steric requirement of the coupling parters, alkenyl stannanes and electrophiles (alkenyl iodides and triflates). The comprehensive survey afforded appropriately matched components for every bond formation considered. Moreover, from the comparison of the reactivities of different coupling partners with different degrees of steric hindrance, the sensitivity of the Stille coupling to steric effects was confirmed. Besides providing a variety of building blocks for retinoid synthesis, the study highlights some trends that might be useful for the application of the Stille reaction to the synthesis of unsubstituted conjugated polyenes.
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 callDisclaimer: 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.
