89885-86-9Relevant academic research and scientific papers
Enantioselective Total Synthesis of the Mycotoxin (-)-Talaromycin B by a Hetero Diels-Alder Reaction
Tietze, Lutz F.,Schneider, Christoph
, p. 2476 - 2481 (2007/10/02)
(-)-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
Baker, Raymond,Boyes, Alastairs L.,Swain, Christopher J.
, p. 1415 - 1421 (2007/10/02)
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.
SYNTHESIS OF (+/-)-TALAROMYCINS A, B, C AND E
Baker, Raymond,Boyes, Alastair L.,Swain, Christopher J.
, p. 985 - 988 (2007/10/02)
Two key unsaturated spiroacetals have been used in the synthesis of talaromycins A, B, C and E by routes involving chlorohydration and reductive dechlorination.
SYNTHESIS OF (-)-TALAROMYCINS A AND B
Mori, Kenji,Ikunaka, Masaya
, p. 45 - 58 (2007/10/02)
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
Kocienski, Philip,Yeates, Clive
, p. 1879 - 1884 (2007/10/02)
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
Midland, M. Mark,Gabriel, Josef
, p. 1143 - 1144 (2007/10/02)
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.
DIASTEREOTOPIC SELECTIVITY AT PROCHIRAL CARBON CENTERS. A STEREODIVERGENT SYNTHESIS OF THE TALAROMYCINS.
Schreiber, Stuart L.,Sommer, Toby J.,Satake, Kunio
, p. 17 - 20 (2007/10/02)
The transformation of the acyclic precursor previously employed in the synthesis of talaromycin B to the stereoisomeric avian toxin talaromycin A is described.Diastereotopic selectivity at prochiral carbon centers in an acetonide migration and in a subseq
SPIROKETALS: A TOTAL SYNTHESIS OF (+/-)-TALAROMYCIN B VIA A STEREOSELECTIVE CATION-OLEFIN CYCLISATION STEP
Kay, I.Trevor,Bartholomew, David
, p. 2035 - 2038 (2007/10/02)
The acid catalysed rearrangement of an acetal derived from 2-hydroxymethyl-3-butene-1-ol proceeding via an intramolecular cation-olefin cyclisation provides acces to a 4-hydroxytetrahydropyran and thence to (+/-)-talaromycin B.
A Synthesis of Talaromycin B
Kocienski, Philip,Yeates, Clive
, p. 151 - 152 (2007/10/02)
The nucleophilic cleavage of the oxirane (4) by the organocuprate derived from 6-lithio-3-ethyl-3,4-dihydro-2H-pyran (3) was the key step in a synthesis of racemic talaromycin B (7).
