79663-49-3

Usage

InChI:InChI=1/C23H30O7/c1-6-18-23(4,26)22(3)20(25)16(29-21(22)30-18)12-10-8-7-9-11-15-14(2)17(27-5)13-19(24)28-15/h7-13,16,18,20-21,25-26H,6H2,1-5H3/b8-7+,11-9+,12-10+/t16-,18-,20+,21+,22+,23+/m1/s1

Upstream product

• 164365-02-0 (1S,3R,4R,5R,6R,7R)-5,6-dimethyl-7-ethyl-3-(hydroxymethyl)-4-(4-methoxybenzyloxy)-2,8-dioxabicyclo[3.3.0]octan-6-ol 
• 536737-79-8 (2S,3R,3aR,4R,5R,6aR)-5-Ethyl-4-hydroxy-3-(4-methoxy-benzyloxy)-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-carbaldehyde 
• 164365-01-9 (1S,3R,4R,5R,6R,7R)-5,6-dimethyl-7-ethyl-4-(4-methoxybenzyloxy)-3-(triisopropylsiloxymethyl)-2,8-dioxabicyclo[3.3.0]octan-6-ol 
• 536737-63-0 (2RS,3R,4R,5R)-3-[(2R,3R)-2,3-dihydroxy-2-pentyl]-5-(triisopropylsiloxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyloxolane 
• 90623-39-5 4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-3(R,S)-(5-hydroxy-6-(4-methoxy-5-methyl-α-pyron-6-yl)-(E,E)-hexa-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane 
• 20843-07-6 3,4-dimethylfuran 
• 536737-87-8 (E)-3-((2R,3R,3aR,4R,5R,6aS)-5-Ethyl-3,4-dihydroxy-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-yl)-propenal 
• 90623-39-5 (1R,3R,4R,5R,6R,7R)-3-ethyl-4,6-dihydroxy-7-<(1E,3E,5RS)-5-hydroxy-6-(4-methoxy-5-methyl-2-pyron-6-yl)hexa-1,3-dienyl>-4,5-dimethyl-2,8-dioxabicyclo<3.3.0>octane 
• 90641-17-1 8(R,S)-ethyl-7(R,S)-hydroxy-5(R,S)-(1(R,S)-hydroxy-6-(phenylsulfinyl)-(E,E)-hexa-2,4-dien-1-yl)-3,3,6(R,S),7-tetramethyl-1(R,S)-2,4,9-trioxabicyclo<4.3.0>nonane 
• 87413-15-8 3-Chloro-benzoic acid (1R,3R,4S,5S,6R)-6-(2-benzyloxy-ethyl)-4-hydroxy-4,5-dimethyl-2,7-dioxa-bicyclo[3.2.0]hept-3-yl ester 
• 87413-17-0 (4R,4aS,5S,6S,7aS)-4-(2-Benzyloxy-ethyl)-6-ethyl-2,2,4a,5-tetramethyl-tetrahydro-furo[2,3-d][1,3]dioxin-5-ol 
• 87413-14-7 (1S,5R,6R)-6-(2-Benzyloxy-ethyl)-4,5-dimethyl-2,7-dioxa-bicyclo[3.2.0]hept-3-ene 
• 87413-21-6 (4S,4aS,5S,6S,7aS)-6-Ethyl-5-hydroxy-2,2,4a,5-tetramethyl-tetrahydro-furo[2,3-d][1,3]dioxine-4-carbaldehyde 
• 87413-20-5 (4R,4aS,5S,6S,7aS)-6-Ethyl-2,2,4a,5-tetramethyl-4-vinyl-tetrahydro-furo[2,3-d][1,3]dioxin-5-ol 

Relevant academic research and scientific papers

Total synthesis of (+)-asteltoxin

A convergent synthesis of (+)-asteltoxin (1) has been achieved by the Horner-Emmons olefination of bis(tetrahydrofuran) aldehyde 53 and α-pyrone phosphonate 5. A key step features the stereoselective construction of a sterically congested quaternary center embedded in the densely functionalized bis(tetrahydrofuran) subunit by a Lewis acid-catalyzed, pinacol-type rearrangement of an epoxy silyl ether. This pivotal rearrangement methodology parallels the proposed biosynthetic pathway of 1 and is ripe for applications to the stereocontrolled synthesis of structurally complex natural products.

TOTAL SYNTHESIS OF (+)-ASTELTOXIN

A total synthesis of (+)-asteltoxin, a novel mycotoxin isolated from Aspergillus stellatus, has been achieved by using D-glucose as an enantiomerically pure starting material.

Total synthesis of (±)-asteltoxin

A convergent synthesis of (±)-asteltoxin has been achieved in 16 steps (3.0% overall yield) from 3,4-dimethylfuran. The attachment of the triene pyrone side chain to the bis(tetrahydrofuran) skeleton proceeds by way of the addition of the Corey equivalent to anion 3 to the aldehyde 2 and a subsequent aldol condensation-dehydration reaction of pyrone 4.