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Université de Neuchâtel

The Synthesis of Natural Acetylenic Compounds from Stereum hirsutum

Fkyerat, Abdellatif ; Dubin, Guy-Marie ; Tabacchi, Raphael

In: Helvetica Chimica Acta, 1999, vol. 82, no. 9, p. 1418-1422

The regioselective synthesis of two new acetylenic compounds, sterehirsutinal (1) and sterehirsutinol (2), isolated recently from culture medium of the fungus Stereum hirsutum, is reported.

Université de Neuchâtel

Asymmetric Synthesis of the cis- and trans-3,4-Dihydro-2,4,8-trihydroxynaphthalen-1(2H)-ones

Couché, Emmanuel ; Fkyerat, Abdellatif ; Tabacchi, Raphael

In: Helvetica Chimica Acta, 2003, vol. 86, no. 1, p. 210-221

A short and efficient protocol for the asymmetric synthesis of cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-one (1 and 2, resp.) is described, with a phthalide annulation as the key step. Introduction of a OH substituent at position 2 was performed by Sharpless dihydroxylation of a silyl enol ether or by means of an...

Université de Neuchâtel

Stereoselective Synthesis of cis- and trans-3,4-Dihydro-3,4,8-trihydroxynaphthalen-1(2H)-one

Couché, Emmanuel ; Fkyerat, Abdellatif ; Tabacchi, Raphael

In: Helvetica Chimica Acta, 2009, vol. 92, no. 5, p. 903-917

A short and efficient protocol for the stereoselective synthesis of racemic trans- and cis-3,4-dihydro-3,4,8-trihydroxynaphthalen-1(2H)-one (1 and 2, resp.), is described, comprising nine and eight steps starting from commercial juglone (=5-hydroxynaphthalene-1,4-dione; 12) (Scheme 4). Furthermore, an attempt to obtain 1 and 2 via...