title: 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.
abstract: 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.
authors.affiliation: School of Pharmacy, Sungkyunkwan University , Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea.
authors.forename: Jin-Seok
authors.initials: JS
authors.lastname: Kim
authors.affiliation: School of Pharmacy, Sungkyunkwan University , Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea.
authors.forename: Yong-Taek
authors.initials: YT
authors.lastname: Lee
authors.affiliation: School of Pharmacy, Sungkyunkwan University , Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea.
authors.forename: Kun-Hee
authors.initials: KH
authors.lastname: Lee
authors.affiliation: School of Pharmacy, Sungkyunkwan University , Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea.
authors.forename: In-Soo
authors.initials: IS
authors.lastname: Myeong
authors.affiliation: School of Pharmacy, Sungkyunkwan University , Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea.
authors.forename: Jong-Cheol
authors.initials: JC
authors.lastname: Kang
authors.affiliation: School of Pharmacy, Sungkyunkwan University , Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea.
authors.forename: Changyoung
authors.initials: C
authors.lastname: Jung
authors.affiliation: School of Pharmacy, Sungkyunkwan University , Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea.
authors.forename: Seok-Hwi
authors.initials: SH
authors.lastname: Park
authors.affiliation: School of Pharmacy, Sungkyunkwan University , Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea.
authors.forename: Won-Hun
authors.initials: WH
authors.lastname: Ham