Stereoselective Chirality Extension of syn,anti- and syn,syn-Oxazine and Stereochemical Analysis of Chiral 1,3-Oxazines: Stereoselective Total Syntheses of (+)-1-Deoxygalactonojirimycin and (−)-1-Deoxygulonojirimycin

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• 作者：Jin-Seok Kim ; Yong-Taek Lee ; Kun-Hee Lee ; In-Soo Myeong ; Jong-Cheol Kang ; Changyoung Jung ; Seok-Hwi Park ; Won-Hun Ham
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：81
• 期：17
• 页码：7432-7438
• 全文大小：428K
• 年卷期：0
• ISSN：1520-6904

文摘

This paper describes the stereoselective total syntheses of (+)-1-deoxygalactonojirimycin and (−)-1-deoxygulonojirimycin via new chiral building blocks syn,anti,syn-oxazine 11a and syn,syn,anti-oxazine 13a. These were accomplished in four steps in 44.1 and 33.7% overall yields, respectively. These chirons were derived from the stereoselective addition of a nucleophile to the corresponding aldehydes of syn,anti-oxazine 10 and syn,syn-oxazine 12. Furthermore, this paper describes the stereochemical analysis of three types of chiral 1,3-oxazines; anti,syn-, syn,anti-, and syn,syn-oxazines using the NOESY technique.