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Olefin Cross‐Metathesis: Studies towards the Total Synthesis of (+)‐Bitungolide F
Authors:Gandrath Dayaker  Palakodety Radha Krishna
Institution:1. D‐211, Discovery Laboratory, Organic & Biomolecular Chemistry Division CSIR‐Indian Institute of Chemical Technology, Hyderabad, 500007, India (phone: +91‐40‐27193158;2. fax:+91‐40‐27160387)
Abstract:A stereoselective synthesis of (5S,6S)‐6‐(2S,5S,7R,8E,10E)‐5‐(benzyloxy)‐7‐{(tert‐butyl)dimethylsilyl]oxy}‐11‐phenylundeca‐8,10‐dien‐2‐yl]‐5‐ethyl‐5,6‐dihydro‐2H‐pyran‐2‐one (=(+)‐9‐O‐benzyl‐11‐O‐(tert‐butyl)dimethylsilyl]bitungolide F) is reported. The strategy involves Gilman reaction, olefin cross‐metathesis, and Horner? Wadsworth? Emmons olefination as key steps.
Keywords:Sharpless epoxidation  Gilman reaction  Grubbs   II catalyst  Olefin cross‐metathesis  Horner  Wadsworth  Emmons olefination
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