Synthesis of Optically Active 14α- and 14β-Cheilanthanic Esters

Nicon Ungur; Veaceslav KulciŢki; Margherita Gavagnin; Francesco Castelluccio; Guido Cimino

doi:10.1055/s-2006-942386

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Synthesis 2006(14): 2385-2391
DOI: 10.1055/s-2006-942386

PAPER

Synthesis of Optically Active 14α- and 14β-Cheilanthanic Esters

Nicon Ungur*^a,b, Veaceslav KulciŢki^a,b, Margherita Gavagnin^a, Francesco Castelluccio^a, Guido Cimino^a
^a Istituto di Chimica Biomolecolare, CNR, Via Campi Flegrei 34, 80078 Pozzuoli (Na), Italy
^b Institutul de Chimie al Academiei de ŞtiinŢe a RM, str. Academiei 3, 2028 Chişinãu, Republic of Moldova
Fax: +373(22)739954; e-Mail: n_ungur@yahoo.co.uk;

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Publication History

Received 8 February 2006
Publication Date:
08 May 2006 (online)

Abstract
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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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