Concise Total Synthesis of Isospongian Diterpenoid (±)‐Polyrhaphin D | Zendy

Wang Zemin | Zendy; Xing Zhimin | Zendy; Liu Lin | Zendy; Zhang Hao | Zendy; Zhong Zhuliang | Zendy; Xie Dr Xingang | Zendy; She  Xuegong | Zendy

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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.

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