Iodine‐Catalyzed Highly Diastereoselective Synthesis of trans‐2,6‐Disubstituted‐3,4‐Dihydropyrans: Application to Concise Construction of C28–C37 Bicyclic Core of (+)‐Sorangicin A |
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| Authors: | Debendra?K Mohapatra Dr Pragna?P Das Manas?Ranjan Pattanayak J?S Yadav Dr |
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| Institution: | 1. Organic Chemistry Division‐I, Indian Institute of Chemical Technology, Council of Scientific & Industrial Research (CSIR), Habsiguda, Uppal Road, Hyderabad‐500007 (India), Fax: (+91)?40‐27160512;2. Indian Institute of Chemical Technology, An Associate Institution of University of Hyderabad, Hyderabad 500 046 (India) |
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| Abstract: | A novel iodine‐catalyzed highly diastereoselective synthesis of trans‐2,6‐disubstituted‐3,4‐dihydropyrans have been achieved from δ‐hydroxy α,β‐unsaturated aldehydes by treating with allyltrimethyl silane in THF at room temperature with good to excellent yields. This methodology has been successfully implemented for a concise asymmetric synthesis of C28–C37 dioxabicyclo3.2.1]octane ring system of (+)‐sorangicin A in 8 steps with 21 % overall yield. |
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| Keywords: | asymmetric synthesis iodine oxygen heterocycles sorangicin A |
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