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

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 ep oxidation-reduction sequence (K-L); (b) the creation of the C3 stereogenic centre by a Pfaltz asymm...

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Bibliographic Details
Published inPerkin 1 : an international journal of organic and bio-organic chemistry no. 19; pp. 2356 - 2366
Main Authors Kocienski, PJ, Pontiroli, A, Qun, L
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONTROLLING BENZYLIC FUNCTIONALITY
OXO KETENE DITHIOACETALS
ROUTE
ELISABETHAE
STEREOCHEMISTRY
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Summary: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 ep oxidation-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 alpha -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.
ISSN:1472-7781
DOI:10.1039/b102961b