83780-27-2

Usage

InChI:InChI=1/C12H22O4/c1-2-9-3-4-12(15-7-9)5-11(14)10(6-13)8-16-12/h9-11,13-14H,2-8H2,1H3/t9-,10+,11+,12-/m1/s1

Upstream product

• 121363-54-0 (3R*,4S*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-9-ethyl-1,7-dioxaspiro<5.5>undecan-4-ol 
• 113195-29-2 (3R,4S,6R,9R)-3-Benzyloxymethyl-9-ethyl-1,7-dioxa-spiro[5.5]undecan-4-ol 
• 73805-43-3 4-Ethyl-5-hydroxypentanoic acid lactone 
• 121363-48-2 (3S*,6R*,9R*)- and (3R*,6R*,9R*)-9-ethyl-3-hydroxymethyl-1,7-dioxaspiro<5.5>undec-4-ene 
• 121363-50-6 2,2-diethyl-5-(6-ethyl-7-hydroxy-3-oxohex-1-yne)-1,3-dioxane 
• 911807-03-9 2-(4-hydroxy-3-hydroxymethylbut-1-ynyl)-5-ethyl-2-methoxytetrahydropyran 
• 121363-53-9 (3R*,4R*,5R*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-5-chloro-9-ethyl-1,7-dioxaspiro<5.5>undecan-4-ol 
• 121363-52-8 (3R*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-9-ethyl-1,7-dioxaspiro<5.5>undec-4-ene 
• 96239-87-1 Toluene-4-sulfonic acid (3R,6R,9R,10S)-9-benzyloxymethyl-10-hydroxy-1,7-dioxa-spiro[5.5]undec-3-ylmethyl ester 
• 87984-86-9 (3R,4S,6R,9S)-3-Benzyloxymethyl-9-hydroxymethyl-1,7-dioxa-spiro[5.5]undecan-4-ol 
• 15990-74-6 3-ethyl-3,4-dihydro-2H-pyran 
• 594-19-4 tert.-butyl lithium 
• 90475-38-0 2,2-dimethy-5-oxiranyl-1,3-dioxane 
• 121363-54-0 (3S*,4S*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-9-ethyl-1,7-dioxaspiro<5.5>undecan-4-ol 

Downstream Products

• 83720-10-9 talaromycin A 
• 83720-10-9 (-)-talaromycin B 
• 106763-16-0 talaromycin A 12-(3',5'-dinitrobenzoate) 
• 106763-16-0 3-(9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecyl)methyl (3',5'-dinitro)benzoate 
• 83720-10-9 talaromycin C 
• 83720-10-9 talaromycin E 
• 83720-10-9 talaromycin F 
• 83720-10-9 talaromycin B 
• 83720-10-9 talaromycin G 
• 113195-31-6 C₂₆H₂₆N₄O₁₄ 
• 106763-16-0 3-(9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecyl)methyl (3',5'-dinitro)benzoate 
• 106763-16-0 3-(9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecyl)methyl (3',5'-dinitro)benzoate 

Relevant academic research and scientific papers

Synthetic studies on spiroketal natural products. V. Total synthesis of (+)-talaromycin A and (-)-talaromycin B

The total synthesis of (+)-talaromycin A and (-)-talaromycin B was accomplished by utilizing a common intermediate (3). The spiroketal (3) was converted to the olefin (4) via thermolysis of the sulfinyl group, C1-unit elongation at the C9-position, and isomerization at the spiro center. On the other hand, 3 was isomerized to 7 at the C9-position and then converted to the olefin (5) in a similar manner to that described for (+)-talaromycin A. These intermediates (4 and 5) were transformed into (+)-talaromycin A and (-)-talaromycin B via addition reaction of trifluoroacetic acid and oxymercuration, respectively.

Enantioselective Total Synthesis of the Mycotoxin (-)-Talaromycin B by a Hetero Diels-Alder Reaction

(-)-Talaromycin B was formed in an overall yield of 5 percent in nine steps via a hetero Diels-Alder reaction of the exocyclic vinyl ether 3 and methyl O-benzoyldiformylacetate (4) as the key transformation.The enantiomerically pure vinyl ether 3 was prep

Synthesis of Talaromycins A, B, C, and E

The synthesis of 2,2-diethyl-5-ethynyl-1,3-dioxane (9) is reported in an overall yield of 27percent from diethyl malonate.Addition of 5-ethyl tetrahydropyran-2-one to the lithium anion of (9) gave the hydroxy ketoacetylene (10) which was converted in four steps to the olefinic spiroacetals (19) and (20), which were obtained in a ratio of 2:1.The individual olefinic spiroacetals (19) and (20) gave access to the (+/-)-talomycins A and C, and B and E via a chlorohydration, reductive dechlorination, and deprotection sequence.

An enantiospecific synthesis of (-)-talaromycins A and B from D-fructose

(3R,4R,5S,6R,9RS)-9-Ethyl-3,4,5-trihydroxy-1,7-dioxaspiroundecane (9) has been synthesised from 2,3;4,5-di-O-isopropylidene-β-D-fructopyranose (3) and transformed into (-)-talaromycin A (1). (-)-Talaromycin B (2) was obtained by isomerisation of 1 in acid medium.

SYNTHESIS OF (+/-)-TALAROMYCINS A, B, C AND E

Two key unsaturated spiroacetals have been used in the synthesis of talaromycins A, B, C and E by routes involving chlorohydration and reductive dechlorination.

ASYMMETRIC INDUCTION BY SULFINYL CHIRALITY. A TOTAL SYNTHESIS OF (+)-TALAROMYCIN A AND (-)-TALAROMYCIN B

A total synthesis of (+)-talaromycin A and (-)-talaromycin B was accomplished by means of successive asymmetric induction of all chiral centers using a chiral sulfinyl group.

SYNTHESIS OF (-)-TALAROMYCINS A AND B

Highly enantiomerically pure (-)-talaromycins A and B undecane> were synthesized starting from chiral building blocks of microbial origin.

New Synthetic Route to Spiroacetals. The 3,4-Dihydro-2H-pyran Approach to (+/-)-Talaromycin B

The nucleophylic cleavage of the oxirane (9) by the organocuprate derived from 3-ethyl-6-lithio-3,4-dihydro-2H-pyran (7) was the key step in a synthesis of racemic talaromycin B (12).A similar synthesis of desethyltalaromycin B (15) from (9) and 6-lithio-

Synthesis of (-)-Talaromycin A

The spiroketal talaromycin A has been prepared in high optical and diastereomeric purity by using a -sigmatropic (Wittig) rearrangement and a -Claisen rearrangement as key steps in controlling absolute configuration.