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

✍ Scribed by Emmanuel Couché; Abdellatif Fkyerat; Raffaele Tabacchi

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 165 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390014

✦ Synopsis

Abstract

A short and efficient protocol for the asymmetric synthesis of cis‐ and trans‐3,4‐dihydro‐2,4,8‐trihydroxynaphthalen‐1(2__H__)‐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 N‐sulfonyloxaziridine. The absolute configuration of each isomer was determined via Mosher‐ester derivatives. By comparison with previously recorded CD spectra of our natural sample, we established that the natural trans‐ and cis‐isomers from Ceratocystis fimbriata sp. platani were the (−)‐(2__S__,4__S__)‐isomer (−)‐2 and the (+)‐(2__S__,4__R__)‐isomer (+)‐1, respectively.