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A General Strategy for the Stereoselective Synthesis of the Furanosesquiterpenes Structurally Related to Pallescensins 1–2

Consiglio Nazionale delle Ricerche (C.N.R.) Istituto di Chimica del Riconoscimento Molecolare, Via Mancinelli 7, 20131 Milano, Italy
Mar. Drugs 2019, 17(4), 245; https://doi.org/10.3390/md17040245
Received: 22 March 2019 / Revised: 16 April 2019 / Accepted: 23 April 2019 / Published: 25 April 2019
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
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Abstract

Here, we describe a general stereoselective synthesis of the marine furanosesquiterpenes structurally related to pallescensins 1–2. The stereoisomeric forms of the pallescensin 1, pallescensin 2, and dihydropallescensin 2 were obtained in high chemical and isomeric purity, whereas isomicrocionin-3 was synthesized for the first time. The sesquiterpene framework was built up by means of the coupling of the C10 cyclogeranyl moiety with the C5 3-(methylene)furan moiety. The key steps of our synthetic procedure are the stereoselective synthesis of four cyclogeraniol isomers, their conversion into the corresponding cyclogeranylsulfonylbenzene derivatives, their alkylation with 3-(chloromethyl)furan, and the final reductive cleavage of the phenylsulfonyl functional group to afford the whole sesquiterpene framework. The enantioselective synthesis of the α-, 3,4-dehydro-γ- and γ-cyclogeraniol isomers was performed using both a lipase-mediated resolution procedure and different regioselective chemical transformations. View Full-Text
Keywords: pallescensin 1; pallescensin 2; dihydropallescensin 2; isomicrocionin-3; pallescensone; furanosesquiterpenes; stereoselective synthesis; lipase-mediated resolution; cyclogeranylsulfonylbenzene isomers pallescensin 1; pallescensin 2; dihydropallescensin 2; isomicrocionin-3; pallescensone; furanosesquiterpenes; stereoselective synthesis; lipase-mediated resolution; cyclogeranylsulfonylbenzene isomers
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Serra, S. A General Strategy for the Stereoselective Synthesis of the Furanosesquiterpenes Structurally Related to Pallescensins 1–2. Mar. Drugs 2019, 17, 245.

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