Premium
Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A
Author(s) -
Chaubet Guilhem,
Goh Shermin S.,
Mohammad Mujahid,
Gockel Birgit,
Cordonnier MarieCaroline A.,
Baars Hannah,
Phillips Andrew W.,
Anderson Edward A.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703229
Subject(s) - butenolide , benzopyran , total synthesis , ring (chemistry) , component (thermodynamics) , natural product , computer science , construct (python library) , stereochemistry , chemistry , programming language , physics , organic chemistry , thermodynamics
Full details of the total synthesis of the Schisandraceae nortriterpenoid natural product rubriflordilactone A are reported. Palladium‐ and cobalt‐catalyzed polycyclizations were employed as key strategies to construct the central pentasubstituted arene from bromoendiyne and triyne precursors. This required the independent assembly of two AB ring aldehydes for combination with a common diyne component. A number of model systems were explored to investigate these two methodologies, and also to establish routes for the installation of the challenging benzopyran and butenolide rings.