Journal
STEROIDS
Volume 201, Issue -, Pages -Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.steroids.2023.109333
Keywords
Cork smoker wash solids; Black wax; Reduction of friedelin; Reduction of 3-acetoxyfriedel-3-en-2-one; Functionalization of friedelane
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Friedelin and 3-acetoxyfriedel-3-en-2-one, known as friedelane triterpenoids, have been isolated from cork smoker wash solids and used as starting materials for the synthesis of new friedelane derivatives. Reduction reactions result in the formation of friedelinol and epi-cerin derivatives.
Friedelin (1) and 3-acetoxyfriedel-3-en-2-one (4), commonly known as friedelane triterpenoids, have been isolated from cork smoker wash solids (also known as black wax) on a multi-gram scale. These compounds are valuable starting materials for the synthesis of new friedelane derivatives. Stereoselective reduction of friedelin by treatment with LiAlH4, sodium, or catalytic hydrogenation results in the formation of both isomers of friedelinol (5 and 7) in excellent yields. Similarly, the reduction of 3-acetoxyfriedel-3-en-2-one gave epi-cerin (14) and a series of isomeric 2,3-diols or alpha-hydroxyketones. These transformations provide the most straightforward and convenient methods for the synthesis of A-ring functionalised friedelane derivatives using easily accessible starting materials.
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