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• 1134474-94-4 (1R,2S,6R)-4,8,8-trimethyl-3-oxo-2-tetrahydropyranyloxy-7,9-dioxabicyclo[4.3.0]non-4-ene 
• 177186-17-3 (1R,4R,8R,9R)-2-hydroxymethyl-6,6,11,11-tetramethyl-5,7,10,12-tetraoxabicyclo<7.3.0.0^9,1>dodec-2-ene 
• 329358-67-0 (3aR,5aR,8aR,8bR)-2,2,4,7,7-pentamethyl-3a,5a,8a,8b-tetrahydrobenzo[1,2-d:3,4-d']bis[1,3]dioxole 
• 1158813-37-6 1D-1,2:5,6-di-O-isopropylidene-3-oxo-4-O-methyl-chiro-inositol 
• 177186-16-2 (1R,2R,3R,4R)-5-formyl-1,2:3,4-di-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetrol 
• 261962-09-8 (tert-butyldimethylsilanyloxy)-(2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid methyl ester 
• 473791-44-5 (2R,3R,4aS,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethoxy-2,3,6-trimethyl-2,3,8,8a-tetrahydro-4aH-benzo[1,4]dioxin-5-one 
• 1352401-14-9 C₂₁H₁₈O₆ 
• 122588-56-1 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran 

Relevant academic research and scientific papers

A divergent strategy to synthesize gabosines featuring a switchable two-way aldol cyclization

Gabosines and their natural analogues, belonging to C7 carbasugars, have attracted great attention in synthesis due to their rich structural variety and promising biological activities. A new diversity-oriented approach for the gabosine-type carbasugars based on a tunable regioselective aldol cyclization of flexible precursor 2 is explored. Two cyclization modes (A and B) of the precursor can be well controlled by switching promoters to selectively produce two resulting cyclohexa(e)nones 3 and 10, both of which are versatile intermediates for various C7 carbasugars. After the conversion of 3 to eight natural carbasugars, the utility of intermediate 10 is illustrated by the first synthesis of (-)-gabosine L, as well as the new synthesis of (-)-gabosine A, (-)-gabosine B, (-)-gabosine N and (-)-gabosine O. The chemical structure and the absolute configuration of (-)-gabosine L are confirmed by its total synthesis.

Carbasugar Synthesis via Vinylogous Ketal: Total Syntheses of (+)-MK7607, (-)-MK7607, (-)-Gabosine A, (-)-Epoxydine B, (-)-Epoxydine C, epi-(+)-Gabosine e and epi-(+)-MK7607

Carbasugars, the carbocyclic analogues of sugars, constitute an important class of natural products with more than 140 members known and have attracted much attention due to their diverse biological activities like anticancer, antibacterial, herbicidal, and various enzyme inhibitory activities. As many carbohydrates are involved in various cellular signaling pathways, there is great interest in synthesis and biological exploration of carbasugars. Herein, we have developed a methodology to install an α,β-unsaturated aldehyde functionality on different inositols and derivatives by vinylogous elimination of the O-protecting group under mildly acidic condition. We have illustrated the versatility and utility of our methodology by the total syntheses of seven carbasugars viz. (-)-MK7607, (-)-gabosine A, (-)-epoxydine B, (-)-epoxydine C, (+)-MK7607, 1-epi-(+)-MK7607 and 1-epi-(+)-gabosine E.

Total synthesis of gabosines via an iron-catalyzed intramolecular tandem aldol process

Several gabosines, belonging to polyhydroxy-cyclohexenone and cyclohexanone class of natural products, are synthesized in various stereoforms using an intramolecular iron-catalyzed tandem aldol process. The reaction, which starts from vinylic pyranoses, i

Concise chemoenzymatic synthesis of gabosine A, ent-epoformin and ent-epiepoformin

An efficient methodology has been developed to synthesize three related enantiomerically pure natural and unnatural compounds, based on a chemoenzymatic approach. We confirmed the usefulness of 3-methyl-cis-1,2-cyclohexadienediol derived from a biotransfo

Syntheses of (-)-gabosine A, (+)-4-epi-gabosine A, (-)-gabosine E, and (+)-4-epi-gabosine e

(+)-4-epi-Gabosine A 1 and (-)-gabosine A 2 have been synthesized starting from methyl α,d-glucopyranoside and methyl α,d-mannopyranoside, respectively, by utilizing Pd(0) catalyzed Stille coupling as the key step. On the other hand, syntheses of (+)-4-ep

Synthesis of gabosine A and N from ribose by the use of ring-closing metathesis

A concise synthetic route is described for the synthesis of gabosine A and N. The key step uses a zinc-mediated tandem reaction where methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-β-D-ribofuranoside is fragmented to give an unsaturated aldehyde which is ally

Syntheses of gabosine A, B, D, and E from allyl sulfide derived from (-)-quinic acid

An efficient conversion of allyl sulfide 6 prepared from (-)-quinic acid (5) to gabosines was achieved by a series of sequential reactions: i) Mislow-Evans rearrangement, ii) SeO2 oxidation, iii) conjugate addition of sodium hydroxide or sodium

A concise and chemoenzymatic synthesis of (-)-gabosine A, a carba-sugar enone from Streptomycetes

The title compound 1 has been prepared, for the first time, in six steps and a completely stereo-controlled fashion from the cis-1,2-dihydrocatechol 3. The starting material is a readily available and enantiopure compound that can be obtained in large qua