2007
DOI: 10.1002/anie.200704024
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Total Syntheses of Amphidinolide H and G

Abstract: General. NMR spectra were recorded with a Bruker DPX 300, AV 400, or DMX 600 spectrometer in the solvents indicated; chemical shifts (δ) are given in ppm relative to TMS, coupling constants (J) in Hertz. The solvent signals were used as references and the chemical shifts converted to the TMS scale (CDCl 3 : δ C = 77.0 ppm; residual CHCl 3 in CDCl 3 : δ H = 7.24 ppm; CD 2 Cl 2 : δ C = 53.8 ppm; residual CH 2 Cl 2 in CD 2 Cl 2 : δ H = 5.32 ppm). Where indicated, the signal assignments are unambiguous; the number… Show more

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Cited by 115 publications
(45 citation statements)
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References 108 publications
(25 reference statements)
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“…Interestingly though, method Bi sessentially restricted to substrates comprising an unprotected hydroxy group at the allylic positionf lanking the tin moiety.E ven alkenylstannanes with an -OH substituent at the homoallylic site were found to react much slower;g ratifyingly,m ethodAis applicable in such cases (entries [15][16][17][18][19].…”
Section: Resultsmentioning
confidence: 93%
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“…Interestingly though, method Bi sessentially restricted to substrates comprising an unprotected hydroxy group at the allylic positionf lanking the tin moiety.E ven alkenylstannanes with an -OH substituent at the homoallylic site were found to react much slower;g ratifyingly,m ethodAis applicable in such cases (entries [15][16][17][18][19].…”
Section: Resultsmentioning
confidence: 93%
“…It is believed that CuTC engenderst ransmetalation of the organotin precursor with formation of ar eactive organocoppers pecies, whereas the added phosphinate serves as essentially neutral tin scavenger that renders the transmetalation irreversible and facilitates the isolation of the product, while not doing any harm even to highly decorated and labile partners.I nt his regard [Ph 2 PO 2 ][NBu 4 ]i ss uperior to fluoride additivesc ommonly used as tin scavengers otherwise, [7,11] which endanger base-labile functionalitya nd, in particular,s ilyl protecting groups that are ubiquitous in target oriented synthesis. [19,20] Prior to the actual application of this methodology to the unprecedented methylation reactione nr oute to 5,6-dihydrocineromycinB( 2), [5] ab rief optimization had been undertaken using stannane 3 as the model compound (Table 1). While this study ultimately furnished the desired product 4 in excellent yield and purity (entry 4), an unexpected correlation of the outcomew ith the order and rate of addition of the different components to the reactionm ixture was observed;t hesep arameters had not been critical in any of the previous applications of the methodology to regular sp 2 -sp 2 Stille/Migitac oupling reactions.…”
Section: Resultsmentioning
confidence: 99%
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“…In a total synthesis of amphidinolides B/D/H/G under way (see the plans for B1 in Scheme 1) 1 we obtained erratic results in a Wittig-like double bond formation. Whereas we had no trouble in preparing fragment C1-C6 and a precursor of fragment C7-C13, fragment C20-C25 posed technical difficulties.…”
mentioning
confidence: 99%
“…One illustration of this point is the fact that no method for preparing the C 9 –C 11 diene in amphidinolides C and F has been reported. A structurally related diene is present in amphidinolides B, G and H. While these compounds have attracted significantly more synthetic attention,10–12 proportionally limited success has been achieved for accessing the key diene motif—likely due to the challenging nature of the metal-mediated cross coupling reaction ( e.g. Suzuki or Stille reaction) commonly envisioned to form dienes 12,13.…”
mentioning
confidence: 99%