Diastereoselective Total Synthesis of the Euphorbia Diterpenoid Pepluanol A: A Reductive Annulation Approach. Issue 30 (27th June 2017)

• Record Type: Journal Article
• Authors: Xuan, Jun; Liu, Zhaobo; Zhu, An; Rao, Peirong; Yu, Lei; Ding, Hanfeng
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 30(2017)
• Page Start: 8898
• Page End: 8901
• Publication Date: 2017-06-27
• Subjects: annulation -- cycloaddition -- regioselectivity -- terpenoids -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201704929
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A new titanium(III)‐catalyzed reductive annulation constructed a series of diversely functionalized 1, 5‐diols in good to excellent yields with respect to a wide scope of vinyl epoxide‐aldehyde substrates. Taken together with a Diels–Alder reaction and a substrate‐controlled diastereoselective cyclopropanation as additional key steps, the synthetic utility of this novel method has been preliminarily explored by the first and concise total synthesis of the Euphorbia diterpenoid (±)‐pepluanol A. Abstract : Full of pep : A new titanium(III)‐catalyzed reductive annulation constructed a series of diversely functionalized 1, 5‐diols in good to excellent yields. With a wide scope of vinyl epoxide‐aldehyde substrates, this method was applied in the first total synthesis of the Euphorbia diterpenoid (±)‐pepluanol A.