- 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.
- Baker, Raymond,Boyes, Alastair L.,Swain, Christopher J.
-
-
Read Online
- 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
- Tietze, Lutz F.,Schneider, Christoph
-
p. 2476 - 2481
(2007/10/02)
-
- 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.
- Baker, Raymond,Boyes, Alastairs L.,Swain, Christopher J.
-
p. 1415 - 1421
(2007/10/02)
-
- SYNTHESIS OF (-)-TALAROMYCINS A AND B
-
Highly enantiomerically pure (-)-talaromycins A and B undecane> were synthesized starting from chiral building blocks of microbial origin.
- Mori, Kenji,Ikunaka, Masaya
-
-
- DIASTEREOTOPIC SELECTIVITY AT PROCHIRAL CARBON CENTERS. A STEREODIVERGENT SYNTHESIS OF THE TALAROMYCINS.
-
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
- Schreiber, Stuart L.,Sommer, Toby J.,Satake, Kunio
-
-
- 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.
- Midland, M. Mark,Gabriel, Josef
-
p. 1143 - 1144
(2007/10/02)
-
- 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-
- Kocienski, Philip,Yeates, Clive
-
p. 1879 - 1884
(2007/10/02)
-
- A Synthesis of Talaromycin B
-
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).
- Kocienski, Philip,Yeates, Clive
-
p. 151 - 152
(2007/10/02)
-
- SPIROKETALS: A TOTAL SYNTHESIS OF (+/-)-TALAROMYCIN B VIA A STEREOSELECTIVE CATION-OLEFIN CYCLISATION STEP
-
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.
- Kay, I.Trevor,Bartholomew, David
-
p. 2035 - 2038
(2007/10/02)
-
- NOC Approach to Spiroketals. A Total Synthesis of (+/-)-Talaromycin B
-
A total synthesis of the unqiue spiroketal natural product talaromycin B (1) is reported.This molecule, produced in nature by the toxicogenic fungus Talaromyces stipitatus, was constructed in the laboratory from the isoxazoline 6 generated (formula) on reacting the oxime 4 with the olefin 5 in the presence of NaOCl/Et3N/H20/CH2Cl2.The synthesis scheme is sufficiently flexible and efficient so as to be of practical use in the preparation of suitable quantities of this material for biological evaluation.
- Kozikowski, Alan P.,Scripko, James G.
-
p. 353 - 355
(2007/10/02)
-
- TOTAL SYNTHESIS OF (+/-)-TALAROMYCIN B
-
The synthesis of (+/-)-talaromycin B is described which employs diastereotopic hydroxymethyl groups in a spiroketalization reaction as a means of controlling remote stereochemical relationships.The acyclic precursor is constucted in a lynchpin process fro
- Schreiber, Stuart L.,Sommer, Toby J.
-
p. 4781 - 4784
(2007/10/02)
-