Total Syntheses of Sarcandrolide J and Shizukaol D: Lindenane Sesquiterpenoid [4+2] Dimers. Issue 2 (2nd December 2016)

• Record Type: Journal Article
• Authors: Yuan, Changchun; Du, Biao; Deng, Heping; Man, Yi; Liu, Bo
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 2(2017)
• Page Start: 637
• Page End: 640
• Publication Date: 2016-12-02
• Subjects: biomimetic synthesis -- cycloaddition -- natural products -- terpenoids -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201610484
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The syntheses of members of a family of lindenane sesquiterpenoid [4+2] dimers led to the total syntheses of sarcandrolide J and shizukaol D. Inspired by a modified biosynthetic pathway, a cascade featuring furan formation/alkene isomerization/Diels–Alder cycloaddition was devised to construct the congested polycyclic architecture of the target molecules with the correct stereochemistry. This study presents a pioneering synthetic entry to this family of natural products and paves the way for fully exploring their biological functions. Abstract : Taking up the challenge : Total syntheses of the title compounds were achieved on the basis of a modified biosynthetic pathway. A conjugated furanyl diene was generated in situ for the first time, and a cascade featuring furan formation/alkene isomerization/Diels–Alder cycloaddition was devised to construct the congested polycyclic architecture of the target molecules.