Journal
HETEROCYCLES
Volume 91, Issue 2, Pages 332-350Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-14-13161
Keywords
Clerodane Diterpene; Diels-Alder Reaction; Enantioselective Synthesis; Natural Product; Total Synthesis
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Funding
- MEXT [25293003]
- Waseda University
- Grants-in-Aid for Scientific Research [25293003] Funding Source: KAKEN
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In this paper, the first total synthesis of (+)-bucidarasins A and C is described. The chiral starting material was successfully obtained via reduction using a CBS catalyst and selective mono-TBS ether formation of trans-2-benzyloxymethy1-2-methylcyclohexane-1,3-diol, which was crucial to the successful enantioselective total synthesis of (+)-bucidarasins A and C. A synthetic approach towards (+)-bucidarasin C, based on the Barton-McCombie protocol, using V-70 as a radical promoter at low temperature to remove the C6-hydroxy moiety is also described.
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