Total Synthesis of Kingianins A, D, and F

A synthesis fit for a king: The total synthesis of (±)‐kingianins A, D, and F has been achieved in ten steps. Key features include the gram‐scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)‐tetraene, the domino 8π–6π electrocyclic ring closure of a (Z,Z,Z,Z)‐tetraene, and...

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Published inAngewandte Chemie International Edition Vol. 52; no. 15; pp. 4221 - 4224
Main Authors Drew, Samuel L., Lawrence, Andrew L., Sherburn, Michael S.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 08.04.2013
WILEY‐VCH Verlag
Subjects
Benzodioxoles - chemical synthesis
Benzodioxoles - chemistry
biomimetic synthesis
domino reactions
Molecular Structure
natural products
Polycyclic Aromatic Hydrocarbons - chemical synthesis
Polycyclic Aromatic Hydrocarbons - chemistry
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
polyynes
radical cations
Stereoisomerism
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Summary:A synthesis fit for a king: The total synthesis of (±)‐kingianins A, D, and F has been achieved in ten steps. Key features include the gram‐scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)‐tetraene, the domino 8π–6π electrocyclic ring closure of a (Z,Z,Z,Z)‐tetraene, and the radical‐cation‐catalyzed formal Diels–Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.
Bibliography:ark:/67375/WNG-2DVMPS7W-G
CNRS
This work was supported by the Australian Research Council. A.L.L. gratefully acknowledges financial support from the Australian Research Council in the form of a Discovery Early Career Researcher Award (DE120102113). S.L.D. gratefully acknowledges financial support from the Rickards family through the Rodney Rickards Scholarship. We thank Prof. Litaudon (CNRS, France) for kindly providing copies of the original NMR data. We also thank Mr. Tony Herlt (ANU) for assistance with HPLC and Mr. Chris Blake (ANU) for NMR measurements.
Australian Research Council - No. DE120102113
istex:C023F59FD2A43280717A0604F3574BE5AEB102B9
ArticleID:ANIE201210084
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201210084