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11. ChemInform Abstract: Enantiospecific Syntheses of Pseudopterosin Aglycones. Part 2. Synthesis of Pseudopterosin K-L Aglycone and Pseudopterosin A-F Aglycone via a B→BA→BAC Annulation Strategy

Author

Liu Qun, Philip J. Kocienski, and Alessandro Pontiroli

Subjects
chemistry.chemical_compound, Annulation, Pseudopterosin A, Allylic rearrangement, Aglycone, Chemistry, Stereochemistry, Ether, General Medicine, Electrophilic aromatic substitution, Sulfone, Stereocenter
Abstract

The enantiomeric aglycones of pseudopterosins K–L and A–F are synthesised from (−)- and (+)-isopulegol respectively. Key features are (a) the construction of the C3 stereogenic centre by a directed epoxidation–reduction sequence (K–L); (b) the creation of the C3 stereogenic centre by a Pfaltz asymmetric conjugate reduction (A–F); (c) benzannulation of a cyclic ketone starting with an α-oxoketene-S,S-acetal to give a tetrahydronaphthol ether; and (d) a diastereoselective intramolecular electrophilic aromatic substitution using an allylic sulfone as the electrophilic trigger to complete the hexahydro-1H-phenalene core. An X-ray structure of compound 50 was determined.

Published
2010

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