Premium
Cover Picture: A Short Synthesis of Clionamine D (Chin. J. Chem. 11/2015)
Author(s) -
Hao Xiang,
Wu Jingjing,
Tian Hailong,
Shi Yong,
Lin Jingrong,
Tian Weisheng
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201590025
Subject(s) - chemistry , lactone , yield (engineering) , chin , stereochemistry , methylene , combinatorial chemistry , organic chemistry , medicine , materials science , metallurgy , anatomy
The cover picture shows a short and efficient synthesis of clionamine D. Steroidal α ‐methylene‐ γ ‐lactones are versatile intermediates for synthesizing related natural products such as clionamines A–D, a family of marine natural alkaloids with potent autophagy bioactivities and unprecedented chemical structures. Employing single oxygen to break the C22‐C23 double bond via a [2+2]/retro‐[2+2] process, Shi and Tian et al . have developed a scalable, four‐step procedure to prepare α ‐methylene‐ γ ‐lactone directly from steroidal sapogenin–needn't prepare dinorcholanic lactone first. A synthesis of clionamine D was therefore achieved in eight steps with an overall yield of 31%. More details are discussed in the article by Tian et al . on page 1235–1238.