400867-98-3

Upstream product

• 112314-06-4 (1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.0^2,6>dodecane 
• 261962-09-8 (tert-butyldimethylsilanyloxy)-(2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid methyl ester 
• 75-36-5 acetyl chloride 
• 90-80-2 D-Glucono-1,5-lactone 
• 1323271-55-1 C₁₈H₃₄O₁₀ 
• 1323271-67-5 C₁₉H₃₆O₉ 

Relevant academic research and scientific papers

Syntheses of (-)-MK7607 and other carbasugars from (-)-shikimic acid

(-)-MK7607 (1) and other carbasugars 2, 3, 4 have been synthesised from (-)-shikimic acid via OsO4-catalysed dihydroxylation of diene 7, an unstable key intermediate which was obtained by transient elimination of triflate 6.

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

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.

Vinylogy in orthoester hydrolysis: Total syntheses of cyclophellitol, valienamine, gabosine K, valienone, gabosine G, 1-epi-streptol, streptol, and uvamalol A

C7-cyclitols represent an important category of natural products possessing a broad spectrum of biological activities. As each member of these compounds is structurally unique, the usual practice is to synthesize them individually from appropriate polyhydroxylated chiral pools. We have observed an unusual vinylogy in acid mediated hydrolysis of enol ethers of myo-inositol 1,3,5-orthoesters giving a synthetically versatile polyhydroxylated cyclohexenal intermediate. We have exploited this unprecedented reaction for developing a general strategy for the rapid and efficient syntheses of several structurally diverse natural products of C7-cyclitol family. We have made an appropriately protected advanced intermediate 25 in five steps from the cheap and commercially available myo-inositol, and this common intermediate has been used to synthesize eight natural products in racemic form. We could synthesize (±)-cyclophellitol in seven steps, (±)-valienamine in five steps, (±)-gabosine I in five steps, (±)-gabosine G in six steps, (±)-gabosine K in three steps, (±)-streptol in six steps, (±)-1-epi-streptol in two steps, and (±)-uvamalol A in five steps from this intermediate.

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

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

The structure and stereochemistry of gabosine K: Syntheses of 7-O-acetylstreptol and 7-O-acetyl-1-epi-streptol

Gabosine K, whose structure was erroneously assigned previously as 7-O-acetyl-4-epi-streptol, has been synthesized for the first time from D-glucose via a key carbocyclization strategy, intramolecular direct aldol reaction of a 2,6-diketone, in 15 steps with 13.5% overall yield. In the same manner, (+)-7-O-acetyl-streptol has been constructed for NMR spectral comparison. The structure, relative and absolute configurations of (-)-gabosine K are now revised and established as (-)-7-O-acetyl-1-epi-streptol, that is, (1R,2S,3S,4R)-tetrahydroxy-5-acetoxymethy lcyclohex-5-ene. Since the specific rotation of the natural product is not available, the absolute configuration of natural gabosine K is either (-)-7-O-acetyl-1-epi-streptol or its enantiomer. Georg Thieme Verlag Stuttgart.

A norbornyl route to cyclohexitols: Stereoselective synthesis of conduritol-E, allo-inositol, MK 7607 and gabosines

A novel fragmentation sequence within the norbornane system, involving C1-C7 bond scission, provides convenient access to a highly functionalized and versatile cyclohexenoid building block which has been further elaborated to a range of cyclohexitols such as, conduritol E, allo-inositol and gabosine B. Our synthesis of the structure corresponding to gabosine K indicates that the structure of this natural product needs to be revised. (C) 2000 Elsevier Science Ltd.