334917-69-0Relevant academic research and scientific papers
Short syntheses of gabosine I and gabosine G from δ-D-gluconolactone
Shing, Tony K. M.,Cheng, Hau M.
, p. 6610 - 6613 (2007)
(Chemical Equation Presented) A short synthesis of gabosine I (1) from δ-D-gluconolactone (3) in four steps, involving a one-pot TPAP oxidation-K2-CO3-mediated intramolecular Horner-Wadsworth-Emmons (HWE) olefination as the key step,
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
Yuan, Po,Liu, Xiaojing,Yang, Xing,Zhang, Yanli,Chen, Xiaochuan
, p. 3692 - 3701 (2017/04/11)
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.
Baylis-Hillman reaction based flexible strategy for the synthesis of gabosine I, gabosine G, epi-gabosine i and carba l-pentose
Radha Krishna, Palakodety,Kadiyala, Raghu Ram
scheme or table, p. 744 - 747 (2012/03/08)
A combination of diastereoselective Baylis-Hillman reaction and RCM reaction set is used as the flexible strategy for the ready access to cyclohexenoid and cyclopentenoid skeletons.
Short and efficient syntheses of gabosine I, streptol, 7-O-acetylstreptol, 1-epi-streptol, gabosine K, and carba α-d-glucose from δ-d-gluconolactone
Shing, Tony K. M.,Chen,Ng
, p. 1318 - 1320 (2011/08/03)
δ-d-Gluconolactone was carbocyclized into an EOM-protected cyclohexenone in four steps involving perethoxymethylation, phosphonate anion addition, reduction, and oxidation with concomitant Horner-Wadsworth-Emmons alkenation. The stable key enone was effic
Carbocyclization of d-glucose: Syntheses of gabosine i and streptol
Shing, Tony K.M.,Chen,Ng, Wai-Lung
, p. 6001 - 6005 (2011/09/19)
d-Glucose was differentially protected with a trans-diacetal at C-2,3, an ethoxymethyl ether at C-4, and a tert-butyldimethylsilyl ether at C-6, and then carbocyclized via a key Horner-Wadsworth-Emmons (HWE) olefination to give a versatile synthetic inter
