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f4-Fmoc-L-alaninef6-Fmoc-D-alanineL-alanineD-alanineOO O NOORf Rf1b: Rf = C4F9 (f4-Fmoc)1c: Rf = C6F13 (f6-Fmoc)(a mixture of 2 compounds)17-mix(a tagged-mixture of L- and D-alanine)17-mixH2NSN OOAllylH2NSN OOAllyl(S)-18(R)-18: (A, B) = (S, S): (A, B) = (S, R): (A, B) = (R, S): (A, B) = (R, R)BAB19b19a19e19g: (A, B) = (S, S): (A, B) = (S, R): (A, B) = (R, S): (A, B) = (R, R)19c19d19f19h(S)-18(S)-18(R)-18(R)-18[b] f-HPLC separationbased on fluorine contentN+C10F21Cl -OTfNHONSONNH HN OOSNABC20b : (A, B, C) = (S, S, S)20c : (A, B, C) = (S, S, R)20f : (A, B, C) = (R, S, R)20h : (A, B, C) = (R, R, R)20d : (A, B, C) = (S, R, R)20a : (A, B, C) = (S, R, S)20e : (A, B, C) = (R, S, S)20g : (A, B, C) = (R, R, S)Fluorouscondensation reagentsplitsplitsplitTenuecyclamide A: 20aEncodewith fluorine contentdeprotectionAll compoundswere synthesized in 52 stepsorandmixture synthesis[a][c]AmacrolactamizationstepsNHONNHOSNNSNOAllylOOHf4-FmocNHONNH OSNNSNOAllylOOHf6-FmocNHON OOHf4/f6-Fmoc?????????????? 18 ??????????????????????????????????????????????????????????????????????f-Fmoc ????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????Scheme 2 ?????? ????????????f-Fmoc ??????????????????????????????????????????????????????????????????Tenuecyclamide A ?? 8 ??????????????????????????????????????????????????1b?????? 1c ?????????????????????????????????????????????????????????????? (Scheme 3, [a])?????????????????????????????????????????????????????????? 17-mix?????????????????????????? (S)-18, (R)-18 ??????????????????????????17-mix ?? 2 ???????????????? (S)-18 ???? (R)-18 ???????????????????????????????????????? 2 ???????????????? (S)-18 ???? (R)-18 ????????????????????????????????????????????????????????????????????????????????????????????????????????8 ???????????????? (20a-h) ???????????? (Scheme 3, [b]) ??????????19a-h ?????????????????????????????????? ?? ?? ?? ?? ?? ?? ?? ?? ?? (6) ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? ?? (Scheme 3, [c]) ??Tenuecyclamide A ?? 8 ???????????????? 20a-h ????????????????????????????????????????????Scheme 3Mix-Ala-OBnMix-Val-OBnMix-Ala-Ala-OBnMix-Ala-Val-OBnMix-Ala-Leu-OBnMix-Val-Ala-OBnMix-Val-Leu-OBnMix-Val-Met-OMe9a-c10a-c11a-c12a-c13a-c14a-c15a-c16a-cDeprotection18 tripeptides1a1b1cf3-Fmoc-Ala-OHf4-Fmoc-Phe-OHf6-Fmoc-Leu-OH8c8a8bMixAla-OHPhe-OHLeu-OHAla-OBnVal-OBnAla-OBnVal-OBnLeu-OBnAla-OBnLeu-OBnMet-OMeSplitf-HPLC separation based onfluorine content－４３－