title: Total synthesis of (+)-Brefeldin A.
abstract: The total synthesis of (+)-brefeldin A has been accomplished via 15 linear steps in a 7.9% overall yield from the known Weinreb amide 6. The key parts of this approach include the stereoselective construction of the cis-disubstituted hydroxycyclopentane skeleton and the direct introduction of the C1-C3 acrylate moiety using a new variant of a trans-vinylogous acyl anion equivalent.
authors.affiliation: College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Kwanak-Gu 151-742, Korea. ygsuh@plaza.snu.ac.kr
authors.forename: Young-Ger
authors.initials: YG
authors.lastname: Suh
authors.forename: Jae-Kyung
authors.initials: JK
authors.lastname: Jung
authors.forename: Seung-Yong
authors.initials: SY
authors.lastname: Seo
authors.forename: Kyung-Hoon
authors.initials: KH
authors.lastname: Min
authors.forename: Dong-Yun
authors.initials: DY
authors.lastname: Shin
authors.forename: Yong-Sil
authors.initials: YS
authors.lastname: Lee
authors.forename: Seok-Ho
authors.initials: SH
authors.lastname: Kim
authors.forename: Hyun-Ju
authors.initials: HJ
authors.lastname: Park
mesh_terms: D000577:Amides / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D020126:Brefeldin A / Q000031:analogs & derivatives / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C465980:4-oxo-brefeldin A; D000577:Amides; D000838:Anions; D020126:Brefeldin A