title: Diastereoselective synthesis of (+)-pseudohygroline via proline-catalyzed alpha-hydroxylation.
abstract: A highly diastereoselective total synthesis of (+)-pseudohygroline (1) starting from D-proline is described using Wittig olefination and MacMillan-alpha-hydroxylation as key reactions. (+)-Pseudohygroline is an important molecule in alkaloid chemistry as it was prepared as part of the first chemical proof of the absolute stereochemistry of biosynthetically important (+)-hygroline (2) and (+)-hygrine (3).
authors.forename: Bheemreddy
authors.initials: B
authors.lastname: Anusha
authors.forename: Ummareddy V Subba
authors.initials: UV
authors.lastname: Reddy
authors.forename: Basireddy V Subba
authors.initials: BV
authors.lastname: Reddy
authors.forename: Cirandur Suresh
authors.initials: CS
authors.lastname: Reddy
mesh_terms: D002384:Catalysis; D006900:Hydroxylation; D011392:Proline / Q000378:metabolism*; D011759:Pyrrolidines / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D011759:Pyrrolidines; C000588747:pseudohygroline; D011392:Proline