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Total Synthesis of (±)‐Englerin A Using An Intermolecular [3+2] Cycloaddition Reaction of Platinum‐Containing Carbonyl Ylide
Author(s) -
Kusama Hiroyuki,
Tazawa Aoi,
Ishida Kento,
Iwasawa Nobuharu
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201500935
Subject(s) - cycloaddition , ylide , chemistry , intermolecular force , stereoselectivity , platinum , total synthesis , octane , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , molecule , financial economics , economics
Total synthesis of (±)‐Englerin A has been achieved starting from γ,δ‐ynone 5 in 14 steps. The key feature of this synthesis is the highly efficient and stereoselective preparation of 8‐oxabicyclo[3.2.1]octane derivative 6 , a core skeleton of Englerin A, based on an inverse electron‐demand [3+2] cycloaddition reaction of the platinum‐containing carbonyl ylide, which was developed in our laboratory.