- Spiroacetal formation through telescoped cycloaddition and carbon-hydrogen bond functionalization: Total synthesis of bistramide A
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Spiroacetals can be formed through a one-pot sequence of a hetero-Diels-Alder reaction an oxidative carbon-hydrogen bond cleavage and an acid treatment. This convergent approach expedites access to a complex molecular subunit which is present in numerous biologically active structures. The utility of the protocol is demonstrated through its application to a brief synthesis of the actin-binding cytotoxin bistramideA.
- Han, Xun,Floreancig, Paul E.
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p. 11075 - 11078
(2015/03/30)
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- Total synthesis of bistramide A and its 36(Z) isomers: Differential effect on cell division, differentiation, and apoptosis
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The total synthesis of bistramide A and its 36(Z),39(S) and 36(Z),39(R) isomers shows that these compounds have different effects on cell division and apoptosis. The synthesis relies on a novel enol ether-forming reaction for the spiroketal fragment, a kinetic oxa-Michael cyclization reaction for the tetrahydropyran fragment, and an asymmetric crotonylation reaction for the amino acid fragment. Preliminary biological studies show a distinct pattern of influence of each of the three compounds on cell division, differentiation, and apoptosis in HL-60 cells, thus suggesting that these effects are independent activities of the natural product. Copyright
- Tomas, Loic,Boije Af Gennaes, Gustav,Hiebel, Marie Aude,Hampson, Peter,Gueyrard, David,Pelotier, Beatrice,Yli-Kauhaluoma, Jari,Piva, Olivier,Lord, Janet M.,Goekjian, Peter G.
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p. 7452 - 7466
(2012/07/28)
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- Total synthesis of bistramide A
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(Chemical Equation Presented) An asymmetric synthesis of the marine metabolite bistramide A is reported. The synthesis relies on the utility of three different organosilane reagents to construct all principle fragments and 8 of the 11 stereogenic centers of the natural product.
- Lowe, Jason T.,Wrona, Iwona E.,Panek, James S.
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p. 327 - 330
(2007/10/03)
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- Stereoselective total synthesis of bistramide A
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(Chemical Equation Presented) A highly stereoselective and convergent total synthesis of bistramide A is described. The salient feature of this synthesis is the construction of the spiroketal subunit by hydrolysis of dialkylated tosylmethyl isocyanide derivative derived via alkylation of TosMIC with suitably substituted halohydrin derivatives.
- Yadav,Chetia, Lakshindra
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p. 4587 - 4589
(2008/03/12)
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- Enantioselective total synthesis of bistramide A
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The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments. Copyright
- Crimmins, Michael T.,DeBaillie, Amy C.
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p. 4936 - 4937
(2007/10/03)
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- Synthesis of bistramide A
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We have developed an efficient and highly stereocontrolled synthesis of bistramide A, a selective activator of protein kinase C isotype δ. Our synthetic strategy featured a novel bidirectional approach for spiroketal construction based on the ring-opening
- Statsuk, Alexander V.,Liu, Dong,Kozmin, Sergey A.
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p. 9546 - 9547
(2007/10/03)
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