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Total Syntheses of Ainsliadimer B and Gochnatiolides A and B
Author(s) -
Xia Dongliang,
Du Yu,
Yi Zhi,
Song Hao,
Qin Yong
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204292
Subject(s) - total synthesis , stereoselectivity , yield (engineering) , derivative (finance) , stereochemistry , chemistry , monomer , organic chemistry , polymer , materials science , catalysis , financial economics , metallurgy , economics
Oh my goch : The total syntheses of ainsliadimer B and gochnatiolides A and B from α‐santonin have been accomplished in 25 steps with approximately 1 % overall yield. A Diels–Alder reaction of natural dehydrozaluzanin C with a monomeric guaianolide derivative allows stereoselective assembly of a dimeric gochnatiolide‐type skeleton with the required stereochemistry and preinstalled functionalities for the synthesis of dimeric ainsliadimer B and gochnatiolides A and B (see scheme).