Chinese Journal of Chemistry

Cover image for Vol. 33 Issue 11

Editors: Guozhen Ji, Shengming Ma

Online ISSN: 1614-7065

Associated Title(s): Chemistry - A European Journal, Chemistry – An Asian Journal, Israel Journal of Chemistry, The Chemical Record

33_11/2015Cover Picture: A Short Synthesis of Clionamine D (Chin. J. Chem. 11/2015)

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.

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