Simple and Productive Total Syntheses of 2‐Deoxy‐streptamine and (±)‐Hyosamine

Abstract

Investigations in connection with the optimization of methods for the synthesis of the dibromoepoxycyclohexenes ( 1 ) and (3)11]-starting materials for the synthesis of trioxatris-o-homobenzenes ("benzene trioxides") (2) and (4)-also revealed a preparatively useful entry to the monobromoepoxycyclohexenes (6) and (7). These bromides, which are readily accessible from benzene in three steps open up-like ( 1 ) and (3)-a number of most promising applications in the field of inositol-like natural products. We report here on the simple total synthesis of the antibiotic building units 2-deoxystreptamine (13)"'and (+)-hyosamine (14)r2. 31; the syntheses are modelled on the synthesis of streptamine from (2)r'l and provide (23) and (14) in excellent yields.Reaction of ( 5 ) with equimolar amounts of N-bromosuccinimide in cc14 affords a mixture of (6) and ( 7 ) (ratio

Síntese e atividade biológica da 2-desoxiestreptamina

“…1,2-anidroconduritol-E [48][49][50] , epi-inositol 51 , 1,4-ciclohexadieno [52][53][54] , ciclopentadieno e p-benzoquinona 55 .…”