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ChemicalBook CAS DataBase List trienomycin A
98873-83-7

trienomycin A synthesis

10synthesis methods
2-Azabicyclo[18.3.1]tetracosa-1(24),6,8,10,16,20,22-heptaen-3-one, 13,15,22-trihydroxy-5-methoxy-14,16-dimethyl-, (5R,6E,8E,10E,13S,14S,15R,16Z)-

117543-72-3
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trienomycin A

98873-83-7
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Yield:-

Steps:

Multi-step reaction with 7 steps
1: CSA
2: 71 percent / i-Pr2EtN / CH2Cl2
3: 95 percent / camphorosulfonic acid / methanol
4: 56 percent / DMAP / CH2Cl2 / -78 °C
5: Et2NH / CH2Cl2 / 0.5 h / 25 °C
6: benzotriazol-1-yloxytris(dimethylamino phosphonium hexafluorophosphate (BOP), Et3N / CH2Cl2
7: 86 percent / TBAF / methanol; tetrahydrofuran

References:

Smith III, Amos B.;Wood, John L.;Wong, Weichyun;Gould, Alexandra E.;Rizzo, Carmelo J.;Barbosa, Joseph;Komiyama, Kanki;Omura, Satoshi [Journal of the American Chemical Society,1996,vol. 118,# 35,p. 8308 - 8315]

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