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NOCHOMeMeGdelavatine A![]()
NCHOMeMeGdelavatine A![]()
BAEOMeOBrBrOCFGDDOMeA Short Synthesis of Delavatine A Unveils New Insights into Site-
Selective Cross-Coupling of 3,5-Dibromo-2-pyrone
Palani, V.; Hugelshofer, C. L.; Kevlishvili, L.; Liu, P.; Sarpong, R.
J. Am. Chem. Soc. 2019, 141, 2652−2660.1-49,106-851112-151) Br2
2) EtONa
3) O3
4) LDA, Tf2O5) Pd(dppf)Cl2, B2pin2
6) (Me3Sn)2CuLi
7) Dibal-H
8) TPAP, NMO9) Pd(PPh3)4, CuI, B
10) Pd(PPh3)4, CuTC, C11) NaCN, then K2CO3, MeI12) TBSOTf, Et3N,
then DBU, PhMe, D
13) LiAlH4
14) (COCl)2, DMSO, Et3N
15) NH4OAc,2) Show the mechanism of step 2.
hint: A cyclopentane is formed5) Which by-product must be avoided ?9) Give the name of steps 9 and 10
10) Show the structure of CuTC11) Show the mechanism of step 11
12) Show the mechanism of step 126) Propose two mechanisms ?![]()
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