title: Total Syntheses of (+)-Gabosine P, (+)-Gabosine Q, (+)-Gabosine E, (-)-Gabosine G, (-)-Gabosine I, (-)-Gabosine K, (+)-Streptol, and (-)-Uvamalol A by a Diversity-Oriented Approach Featuring Tunable Deprotection Manipulation.
abstract: A new diversity-oriented approach to C7-cyclitols, which possess a broad spectrum of biological activities, is developed. The key polyoxygenated intermediates with different O-protecting groups were accessed by an intramolecular aldol-cyclization of a diketone derived from δ-d-gluconolactone. The versatile intermediates can be easily transformed into structurally different carbasugars based on control of deprotection manipulation. The utility of the robust approach is illustrated by the first syntheses of (+)-gabosines P and Q, as well as the syntheses of several other gabosines and related analogues viz. (+)-gabosine E, (-)-gabosine G, (-)-gabosine I, (-)-gabosine K, (+)-streptol, and (-)-uvamalol A. In addition, the absolute configuration of (-)-uvamalol A is assigned by its total synthesis.
authors.affiliation: Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, PR China.
authors.forename: Po
authors.initials: P
authors.lastname: Yuan
authors.affiliation: Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, PR China.
authors.forename: Xiaojing
authors.initials: X
authors.lastname: Liu
authors.affiliation: Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, PR China.
authors.forename: Xing
authors.initials: X
authors.lastname: Yang
authors.affiliation: Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, PR China.
authors.forename: Yanli
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, PR China.
authors.forename: Xiaochuan
authors.identifier: 0000-0003-3901-0524
authors.initials: X
authors.lastname: Chen
mesh_terms: D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003512:Cyclohexanones