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Synthesis of the Major Oxepane Segment of Zoapatanol
Authors:Jhillu S Yadav  Uttam Dash  Nagesh Guguloth  Debendra K Mohapatra
Institution:1. Natural Products Chemistry Division, CSIR‐Indian Institute of Chemical Technology, Hyderabad‐500007, India (phone: +91‐40‐27193128;2. fax: +91‐40‐27160512)
Abstract:A linear synthesis of the major oxepane fragment of zoapatanol, showing the induction of uterine contractions, and cervical dilation and uterine bleeding (by the concentrated zoapatle tea) in early human pregnancy, isolated from the leaves of Mexican zoapatle plant Montanoa tomentosa, is described from known intermediate involving Sharpless asymmetric epoxidation, bis‐epoxide opening reaction with Corey? Chaykovsky reagent, ring‐closing metathesis reaction, and Horner? Wadsworth? Emmons olefination reaction as key steps.
Keywords:Asymmetric synthesis  Wittig olefination  Sharpless asymmetric epoxidation  Horner?Wadsworth?Emmons olefination  Ring‐closing metathesis  Oxepane  Zoapatanol
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