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Concise Total Synthesis of Isospongian Diterpenoid (±)‐Polyrhaphin D
Author(s) -
Wang Zemin,
Xing Zhimin,
Liu Lin,
Zhang Hao,
Zhong Zhuliang,
Xie Dr Xingang,
She Xuegong
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600635
Subject(s) - butenolide , total synthesis , aldol reaction , chemistry , ring (chemistry) , stereochemistry , terpenoid , intramolecular force , olefin fiber , ketone , yield (engineering) , isomerization , derivative (finance) , organic chemistry , catalysis , physics , financial economics , economics , thermodynamics
The first total synthesis of isospongian diterpenoid (±)‐polyrhaphin D has been accomplished in 9 steps with 19 % overall yield starting from the Wieland–Miescher ketone derivative. The key features of our synthesis include a sequential reduction/Michael addition/aldol condenzation to assemble the A ring and an intramolecular dehydrative cyclization/olefin isomerization reaction to install the γ‐butenolide D ring.