title: Chirality extension of an oxazine building block en route to total syntheses of (+)-hyacinthacine A2 and sphingofungin B.
abstract: Concise and stereocontrolled syntheses of (+)-hyacinthacine A2 and sphingofungin B were achieved via a diastereomerically enriched oxazine intermediate. The key strategies include palladium(0)-catalyzed intramolecular oxazine formation and diastereoselective nucleophilic addition to an aldehyde. (+)-Hyacinthacine A2 was synthesized in 13 steps and 10.2% overall yield and the synthesis of sphingofungin B proceeded in a linear sequence over 15 steps and 6.9% overall yield from (R)-methyl 2-benzamido-3-((tert-butyldimethylsilyl)oxy)propanoate.
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea. whham@skku.edu.
authors.forename: Seok-Hwi
authors.initials: SH
authors.lastname: Park
authors.forename: Xiangdan
authors.initials: X
authors.lastname: Jin
authors.forename: Jong-Cheol
authors.initials: JC
authors.lastname: Kang
authors.forename: Changyoung
authors.initials: C
authors.lastname: Jung
authors.forename: Seong-Soo
authors.initials: SS
authors.lastname: Kim
authors.forename: Sung-Soo
authors.initials: SS
authors.lastname: Kim
authors.forename: Kee-Young
authors.initials: KY
authors.lastname: Lee
authors.forename: Won-Hun
authors.initials: WH
authors.lastname: Ham
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D001232:Aspergillus fumigatus / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis / Q000737:chemistry; D019668:Liliaceae / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001688:Biological Products; D005231:Fatty Acids, Unsaturated; D010078:Oxazines; D011763:Pyrrolizidine Alkaloids; C500284:hyacinthacine A2; C076078:sphingofungin B; D010165:Palladium