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13-15OOOOHHOOCO2MeSeSePhOSiOTBSOHOOOOOHHOOSnSnMe3A biomimetic total synthesis of (+)-intricarene
Tang, B.; Bray, C. D.; Pattenden G.
Tetrahedron Lett. 2006, 47, 6401–6404.1) TMS-acetylene, n-BuLi, BF3•OEt2,
-78°C to -30°C
2) K2CO3
3) Cp2ZrCl2, AlMe3, r.t., then reflux
then I2, -30°C
4) TsCl, pyridine
5) K2CO3
6) 1, NaHMDS, -78°C
then substrate, BF3•OEt2, 0°C
7) p-TSA
8) H2O2, 0°C
9) PPTS (cat.)
10) 2, Pd(PPh3)4, CuI, CsF(+)-intricarene3) Hint: Isomerization occurs upon reflux.1(+)-Intricarene(–)-Bipinnatin J11) Ph3P, NBS
12) CrCl213) VO(acac)2, t-BuOOH, -20°C
14) Ac2O, Et3N, DMAP (cat.)
15) DBU, reflux215) Please classify the reaction and classify and draw its key intermediate. Hint: an ylide is formed.12) These conditions were a precursor to a named coupling reaction. Name this reaction and identify the missing co-catalyst.10) Please name the reaction.1) Please name the starting material.![]()
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