. Acide, -bromométhyl)acrylique 253a, DIAD, PPh 3 , Et 2 O, t.a, 64% ; b. Grubbs II, CH 2 Cl 2 , reflux, 2 h, 91%. DIAD = azodicarboxylate de diisopropyle

. Etoac, the desired lactone 267 as a yellow oil (122.5 mg, 0.38 mmol, 49%)

. Etoac, R f =0 1 H-NMR (400 MHz, CDCl 3 , 25 °C): ? 7.16 (bs32 (s, 1H, 393 (s, 1H, 3''-H), 5.79 (ddd, J=17.3, 10.6, 6.4 Hz, the desired ester 278-I as a yellow oil (47.6 mg J=10.6 Hz, 1H, 1-H), 4.93-4.88 (m, 1H, 7-H), 4.63H) ppm. 13 C-NMR (100 MHz, CDCl 3 , 25 °C): ? 173.6 (C=O), pp.27-150, 2019.

I. Grubbs, 15 equiv) was added to a solution of ester 278-I (47.6 mg, 0.11 mmol, 1.0 equiv) in CH 2 Cl 2 (11 mL, 0.01 M) The mixture was heated to reflux for 1 hour. DMSO (40 µL, 50 equiv/catalyst) was then added at room temperature and the mixture was stirred for 12 hours. Evaporation of the solvent under reduced pressure followed by flash chromatography, 38%). R f =0, p.8025

I. Grubbs, 30 equiv) was added to a solution of compound 323a (30 mg, 55 µmol, 1.0 equiv) in CH 2 Cl 2 (500 mL, 0.1 mM) at reflux. The mixture was stirred for 12 hours. Evaporation of the solvent under reduced pressure followed by flash chromatography (SiO 2 , 90/10 pentane/Et 2 O) yielded the desired cyclic compound 324a as a yellow oil, p.1

. Mhz, 25 °C): ? 6.39 (s, 1H, pp.88-89

1. Hz, 74 (s, 1H, p.47

I. Grubbs, 30 equiv) was added to a solution of compound 323b (110 mg, 0.19 mol, 1.0 equiv) in CH 2 Cl 2 (2 L, 0.1 mM) at reflux. The mixture was stirred for 12 hours. Evaporation of the solvent under reduced pressure followed by flash chromatography (SiO 2 , 90/10 pentane/Et 2 O) yielded the desired cyclic compound 324b as a yellow oil (34 mg, 63 µmol, 33%), p.1

. Mhz, 08 (s, 1H70 (s, 1H, 5.89 (td, J=10.4, 6.9 Hz (t, J=10.4 Hz, 1H, pp.47-52

. Etoac, 6 µmol, 49% over 2 steps) R f =0, EtOAc). 1 H-NMR (400 MHz, CDCl 3 , 25 °C): ? 7.26 (bs, 1H, 8-H), 6.43 (d, J=2.4 Hz, 1H (m, 2H, 2-H, 1-H), 5.37 (dt, J=8.2, 1.8 Hz, pp.59-64

. Etoac, 14 (bs, 1H66 (bs, 1H, 5''-H), 5.60-5.46 (m, 2H, 2-H, 1-H), 5.38 (ddd, the desired lactone 325b as a colorless oil (5.6 mg, 17 µmol, 52% over (t, J=1.7 Hz 5.78 (d, J=2.4 Hz, 1HH), 4.73 (dd, J=10.4, 3.4 HzH), 2.81 (dd, J=14.5, 11.1 Hz, pp.6-37

. Mhz, CDCl 3 , 25 °C): ? 176

. Pentane, Et 2 O), the desired ester 330c as a pale yellow oil with the side-product 330c

. Hz, 20 (s, 2H, 1'-CH 2 Br) ppm. 13 C-NMR (100 MHz

I. Grubbs, 72 µmol, 0.30 equiv) was added by portions to a refluxing solution of ester 330a (50 mg, 0.24 mmol, 1.0 equiv) in CH 2 Cl 2 (50 mL, 5 mM) over 2 hours. The mixture was then filtered, p.68

2. ). ?mol, 1 H-NMR (400 MHz, CDCl 3 , 25 °C): ? 7, p.1

. Ppm, 13 C-NMR (100 MHz, CDCl 3 , 25 °C): ? 171, pp.70-71

I. Grubbs, 20 equiv) was added by portions to a refluxing solution of ester 330b (308 mg, 1.3 mmol, 1.0 equiv) in CH 2 Cl 2 (130 mL, 0.01 M) over 1 hour. The mixture was then filtered on silica (SiO 2 , 80/20 pentane/Et 2 O) and the evaporation of the solvant yielded the desired ester 331b (191 mg, 0.87 mmol, 70%). R f =0, °C): ? 151.1 (C-3), pp.61-67

I. Grubbs, 15 equiv) was added by portions to a refluxing solution of esters 330c and 330c' (702.8 mg, 2.5 mmol, 1.0 equiv) in CH 2 Cl 2 (250 mL, 0.01 M) over 1 hour. The mixture was then filtrated on silica (SiO 2 , 80/20 pentane/Et 2 O) and the evaporation of the solvant yielded the desired ester 331c (290 mg, 1.1 mmol, 46%, pp.92-330

. Fmoc-cys, Mmt)-OH. Mmt deprotection of the cysteine residue was performed following the general procedure

. Fmoc-cys, Phe-Phe-Rink Amide resin 380a Resin 380a was prepared from resin 379 following the general procedure

. Fmoc-cys, Maltose)-Phe-Phe-Rink Amide resin 380h Resin 380h was prepared from resin 379 following the general procedure

2. Hz, (s, 3H), 1.94 (s, 3H) ppm. 13 C-NMR (100 MHz, CDCl 3 , 25 °C): ? 173, 1H), 5.25 (t, J=10.0 Hz, 1H), 5.10 (m, 1H), 4.71 (m, 1H), 4.60 (d, J=10.0 Hz, 1H, 1-H?), 4.54-4.45 (m, 2H), 4.19-4.04, pp.67-73, 2000.

1. Hz, 02 (s, 3H), 1.91 (s, 3H), 1.15 (d, J=6.5 Hz, 3H) ppm. 13 C-NMR (100 MHz, CDCl 3 , 25 °C): ? 173, ×2), 129.1 (×2)

1. Hz, (s, 3H), 1.94 (s, 3H) ppm. 13 C-NMR (CDCl 3 , 100 MHz, 25 °C): ? 173, 4.08 (m, 1H), 3.80-3.68 (m, 2H), 3.63 (m, 1H) 3H), 2.07 (s, 6H), 2.05 (s, 3H), 2.01 (s, 3H), pp.4-55

. Fmoc-cys, Ala-Pro-Pro-Ala-Rink Amide resin IIIa Resin IIIa was prepared from resin II following the general procedure

. Fmoc-cys, Arg(Pbf)-Pro-Ala-Pro-Gly-Ser(t-Bu)-Cys(perOAc-Lactose)-Ala- Pro-Pro-Ala-Rink Amide resin VIbb Resin VIbb was prepared from resin Vb following the general procedure

. Fmoc-cys, Arg(Pbf)-Pro-Ala-Pro-Gly-Ser(t-Bu)-Cys(perOAc- Glucose)-Ala-Pro-Pro-Ala-Rink Amide resin VIIaa Resin VIIaa was prepared from resin VIaa following the general procedure

. Fmoc-cys, Arg(Pbf)-Pro-Ala-Pro-Gly-Ser(t-Bu)-Cys(perOAc- Glucose)-Ala-Pro-Pro-Ala-Rink Amide resin VIIab Resin VIIab was prepared from resin VIab following the general procedure

. Fmoc-his, Trt)-Gly-Val-Thr(t-Bu)-Ser(t-Bu)-Ala-Pro-Asp, p.-Cys

. Arg, Pro-Ala-Pro-Gly-Ser(t-Bu)-Cys(perOAc-Lactose)-Ala-Pro-Pro-Ala-Rink Amide resin VIIIbb Resin VIIIbb was prepared from resin VIIbb following the general procedure (5) using successively Fmoc-Asp(t-Bu)-OH, Fmoc-Pro-OH

. Fmoc-thr, OH, Fmoc-Val-OH, Fmoc-Gly-OH and Fmoc-His(Trt)-OH

. Fmoc-his, Trt)-Gly-Val-Thr(t-Bu)-Ser(t-Bu)-Ala-Pro-Asp

. Pro-gly-ser, Cys-Ala-Pro-Pro-Ala-Rink Amide resin IX Resin IX was prepared from NovaPEG Rink amide resin (100 mg, p.20

O. , F. , and F. Fmoc-arg, Pbf)-OH, Fmoc-Cys(Mmt)-OH, Fmoc-Asp(t- Bu)-OH, Fmoc-Pro-OH, OH, Fmoc-Thr(t-Bu)-OH

. Val-oh, Fmoc-Gly-OH and Fmoc-His(Trt)-OH. Mmt deprotection of the cysteine residues was performed following the general procedure

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