First Total Synthesis of Prionoid E,A Bioactive Rearranged Secoabietane Diterpene Quinone from Salvia prionitis |
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| Authors: | Fei Deng Jun Xu Min Zhao Hong‐Ying Liu Yang Ye Jin‐Sheng Zhang |
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| Institution: | 1. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, P.?R. China, (phone: +86‐21‐50805892;2. fax: +86‐21‐50807088);3. College of Life Sciences, Northwest A & F University, Yangling 712100, P.?R. China |
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| Abstract: | The first total synthesis of prionoid E ( 1 ), a rearranged secoabietane diterpene quinone isolated from Salvia prionitis, was achieved efficiently by means of Wacker oxidation (Scheme 5) and aldol condensation (Scheme 7) as the key steps in the synthetic sequence. Thus 1 was prepared in 15 steps in 3.7% yield starting on one hand from anisole (=methoxybenzene) and methylsuccinic anhydride (=dihydro‐3‐methylfuran‐2,5‐dione) via 4 (Scheme 3 and 5), and on the other hand from 2‐hydroxy‐2‐methylpropanoic acid via 5 (Scheme 6). |
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| Keywords: | Salvia prionitis Prionoid E Secoabietanes Quinones Diterpene quinones Wacker oxidation |
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