Reaction SMILES: [F:1][C:2]([F:16])([F:15])[C:3]([O:13][CH3:14])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:32][C@H:33]1[CH2:64][C:63]([CH3:65])=[CH:62][C@@H:61]([CH2:66][CH:67]=[CH2:68])[C:59](=[O:60])[CH2:58][C@H:57]([OH:69])[C@@H:56]([CH3:70])[C@@H:55](/[C:71](/[CH3:82])=[CH:72]/[C@H:73]2[CH2:78][C@@H:77]([O:79][CH3:80])[C@H:76](O)[CH2:75][CH2:74]2)[O:54][C:52](=[O:53])[C@H:51]2[N:46]([CH2:47][CH2:48][CH2:49][CH2:50]2)[C:44](=[O:45])[C:42](=[O:43])[C@:40]2([OH:83])[O:41][C@@H:36]([C@@H:37]([O:85][CH3:86])[CH2:38][C@H:39]2[CH3:84])[C@@H:35]([O:87][CH3:88])[CH2:34]1>C(OCC)(=O)C.CN(C1C=CN=CC=1)C.C(OCC)C>[CH2:66]([CH:61]1[CH:62]=[C:63]([CH3:65])[CH2:64][CH:33]([CH3:32])[CH2:34][CH:35]([O:87][CH3:88])[CH:36]2[O:41][C:40]([OH:83])([CH:39]([CH3:84])[CH2:38][CH:37]2[O:85][CH3:86])[C:42](=[O:43])[C:44](=[O:45])[N:46]2[CH:51]([CH2:50][CH2:49][CH2:48][CH2:47]2)[C:52](=[O:53])[O:54][CH:55]([C:71]([CH3:82])=[CH:72][CH:73]2[CH2:74][CH2:75][CH:76]([O:5][C:4](=[O:6])[C:3]([C:2]([F:15])([F:16])[F:1])([O:13][CH3:14])[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:77]([O:79][CH3:80])[CH2:78]2)[CH:56]([CH3:70])[CH:57]([OH:69])[CH2:58][C:59]1=[O:60])[CH:67]=[CH2:68]
Reactant: C=CC[C@@H]1C=C(C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC
Reactant: COC(C(=O)O)(c1ccccc1)C(F)(F)F
Agent: C(=NC1CCCCC1)=NC1CCCCC1
Agent: C=CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC
Agent: CN(C)c1ccncc1
Solvent: CCOC(C)=O
Solvent: CCOCC
Product: C=CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(OC(=O)C(OC)(c4ccccc4)C(F)(F)F)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC
Temperature: 25 °C
Reaction time: 1.5 h

Procedure:
To a solution of (−)-2-trifluoromethyl-2-methoxy-2-phenylacetic acid (51 mg) in ethyl acetate (10 ml) was added at room temperature N,N′-dicyclohexylcarbodiimide (47 mg). After stirring for 1.5 hours at room temperature, then the FR-900506 substance (25.0 mg) and 4-(N,N-dimethylamino)-pyridine (11 mg) were added, followed by stirring at room temperature for 3.5 hours. The resulting solution was concentrated to provide a residue, which was taken up in diethyl ether and then washed successively with hydrochloric acid, an aqueous sodium hydrogen carbonate and an aqueous sodium chloride. The organic layer was dried over sodium sulfate and concentrated to provide a residue, which was chromatographed on silica gel (developing solvent: dichloromethane and diethyl ether, 10:1 v/v) to give 17-allyl-12-[2-[4-[(−)-2-trifluoromethyl-2-methoxy-2-phenylacetoxy]-3-methoxycyclohexyl]-1-methylvinyl]-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (6.5 mg) and 17-allyl-14-[(−)-2-trifluoromethyl-2-methoxy-2-phenylacetoxy]-12-[2-[4-[(−)-2-trifluoromethyl-3-methoxy-3-phenylacetoxy]-3-methoxycyclohexyl]-1-methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo-[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (20.2 mg).