Total synthesis of cis-shisool

• 出 处: Chinese Journal of Chemistry
• 发表日期: 1990年01期
• 关键词: isomers carbonyl elucidated saturated attributed remove hydroxide dried silica h

This paper describes the total sythesis of cis-shisool through intermediate 3,which wasderived from the Diels-Alder adduct 4(or 5).The structure of the isomers produced by the Diels-Alderreaction of cyclohexadiene and crotonate has been elucidated by means of GC and NMR.Methylena-tion of 12 with Zn-CH_2Br_2-TiCl_4 or Ph_3P=CH_2 retains the stereochemistry of the carbon atom ad-jacent to the carbonyl group.

This paper describes the total sythesis of cis-shisool through intermediate 3, which was derived from the Diels-Alder adduct 4 (or 5). The structure of the isomers produced by the Diels-Alder reaction of cyclohexadiene and crotonate has been elucidated by means of GC and NMR. Methylen-tion of 12 with Zn-CH_2Br_2-TiCl_4 or Ph_3P = CH_2 retains the stereochemistry of the carbon atom ad-jacent to the carbonyl group.