Abstract
A diastereoselective approach to polyoxygenated atisene-type diterpenes starting from ( S)-(+)-carvone is described. The key steps used in the preparation of the atisene framework are an intramolecular Diels–Alder reaction, an intramolecular diazoketone cyclopropanation, an endocyclic cyclopropane ring cleavage and the regioselective reduction of an allylic bromide by a low-valent chromium species. The synthesis of natural atisanes antiquorin ( 1), atis-16-ene-3,14-dione ( 3), atis-16-ene-2,3,14-trione ( 8) and 3β-hydroxy-atis-16-ene-2,14-dione ( 9) following this approach is presented. Also described is the synthesis of 18-hydroxy-atis-16-ene-3,14-dione ( 5), the structure erroneously assigned to an atisene isolated from the Fijian plant Euphorbia fidjiana. This work shows that the natural atisene isolated from this plant is, in fact, the epimer at C-4 of this compound.
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.
