Euryfuran

Scheme 19.13 Euryfuran via a sequential furan ring transfer.

Methoxy(phenylthio)methane and methoxy(phenylsulfonyl)methane are useful fonnyl anion equivalents for one-carbon homologation. For instance, addition of methoxy(phenylthio)methyllithium to ketones, followed by rearrangement of the adduct, provides a new method for the preparation of a-(phe-nylthio) aldehydes (equation 39). The rearrangement is stereospecific. This meAod has been used for the total synthesis of annelated furans such as (+)-euryfuran, butenolides such as isoderminin and con-fertifolin and spirocyclic tetrahydrofiirans and butenolides. ... 

This type of chemistry was applied to the synthesis of euryfuran and xestoquinone , as well as spongiaditerpenoids. 

Ftirodysinine (60) and euryfuran (52) have been identified as feeding deterrents in nudibranchs (78, 80, 524, 525). Deterrent activity has also been reported for pallescensin (50), idiadione (156), the isonitrile 769, and the isothiocyanate 770 (524). These compounds were also toxic to goldfish at 0.1 mg/mL. Axisonitrile (771) was ineffective as antifeedant, but showed strong ichthyotoxicity, the minimum active concentration being at 8 ppm. Furoscalarol (772) and deoxoscalarin (773) were active in the feeding inhibition bioassay (526). 

Kanematsu, K. and Soejima, S. (1991) Total synthesis of euryfuran via two sequential furan ring transfer reaction. Heterocydes, 32, 1483-1486. 

Hypselodoris zebra Euryfuran Dysidea herbacea erode and Cardellina, 1984... 

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