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Synthesis 2006(14): 2385-2391
DOI: 10.1055/s-2006-942386
DOI: 10.1055/s-2006-942386
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Optically Active 14α- and 14β-Cheilanthanic Esters
Weitere Informationen
Received
8 February 2006
Publikationsdatum:
08. Mai 2006 (online)
Publikationsverlauf
Publikationsdatum:
08. Mai 2006 (online)
Abstract
Isomeric cheilanthane sesterterpenoids have been obtained stereospecifically by two different synthetic pathways. Superacidic, low-temperature cyclization of C25 substrates (13E-bicyclogeranylfarnesoic acid methyl esters) led to 14α-cheilanthanes , along with other compounds, whereas the side-chain extension of a C20 precursor (ent-isocopalic alcohol) afforded 14β-cheilanthanes. The synthesized compounds could be considered as useful synthons in the preparation of bioactive natural cheilanthanes and structurally related sesterterpenoids.
Key words
terpenoids - cyclizations - rearrangements - synthesis - esters
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