Abstract
A formal synthesis of (−)-isoavenaciolide (1) by two different routes is reported. The first approach, leading to a key precursor 2 of (−)-isoavenaciolide (1), features the stereoselective construction of the three contiguous stereogenic centers by Evans diastereoselective reduction (d.e. = 80%) of β-hydroxy ketone 8. In the more efficient second approach, the nine-step sequence leading to the key precursor 2 involves sequential ruthenium-catalyzed hydrogenation reactions of β-keto ester 4 and β-hydroxy ketone 14 to form the two hydroxyl groups with an excellent control of the anti stereochemistry (d.e. = 99%). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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.
