Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A

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...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-10, Vol.23 (56), p.14080-14089
Main Authors: Chaubet, Guilhem, Goh, Shermin S., Mohammad, Mujahid, Gockel, Birgit, Cordonnier, Marie‐Caroline A., Baars, Hannah, Phillips, Andrew W., Anderson, Edward A.
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemistry
cascade cyclization
Catalysis
Cobalt - chemistry
Cyclization
cyclotrimerization
Magnetic Resonance Spectroscopy
natural products
Palladium - chemistry
Schisandraceae - chemistry
Schisandraceae - metabolism
Stereoisomerism
total synthesis
transition-metal catalysis
Triterpenes - chemical synthesis
Triterpenes - chemistry
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Summary: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. Total terpenoids: The total synthesis of the Schisandraceae nortriterpene rubriflordilactone A is reported. Palladium‐ and cobalt‐catalyzed polycyclizations were employed as key strategies to construct the central arene D ring from bromoendiyne and triyne precursors. 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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201703229