SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 15, 2008, Pages 2379-2383

Total synthesis of largazole

(6) Ren, Qi a Dai, Lu a Zhang, Hui a Tan, Wenfei a Xu, Zhengshuang a,b Ye, Tao a,b

a PEKING UNIVERSITY (China)

b HONG KONG POLYTECHNIC UNIVERSITY (Hong Kong)

Author keywords

Antitumor; Cyclodepsipeptide; Largazole; Macrolactamization; Total synthesis

Indexed keywords

LARGAZOLE; PYRROLE DERIVATIVE; THIAZOLE DERIVATIVE; THIAZOLIDINETHIONE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 52949112287 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078270 Document Type: Article

Times cited : (81)

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- Procedure for the Preparation of Intermediate 13 (R)-3-Acetyl-4-isopropyl-1,3-thiazolidine-2-thione (12, 821 mg, 4.0 mmol) was dissolved in CH2Cl2 (10 mL, TiCl 4 (751 mg, 4.0 mol) was added at 0°C After 5 min, the reaction was brought to -78°C, DIPEA (516 mg, 4.0 mmol) was added via a syringe over 10 min. The reaction was kept at -78°C for 2 h before aldehyde 11 (428.3 mg, 2.0 mmol) in CH2Cl2 (3 mL) was added dropwise. Saturated NH4Cl (20 mL) was added to the reaction mixture and CH 2Cl2 (3 x 30 mL) was used for extraction. The combined organic phases were dried over anhyd MgSO4 and concentrated in vacuo to give the crude product, which was purified by chromatography on SiO 2, eluting with EtOAc-hexane (1:8, to afford the desired compound 13 (692.1 mg, 83, along with the minor isomer 53.2 mg, 6
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53
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- Cyclodepsipeptide 20 [α]D20 17.5 (c 0.2, MeOH, 1H NMR (500 MHz, CDCl3, δ, 7.75 (s, 1 H, 7.18 (d, 1 H, J, 9.3 Hz, 6.50 (dd, 1 H, J, 2.7, 9.0 Hz, 5.88 (dd, 1 H, J, 6.9, 14.6 Hz, 5.65-5.71 (m, 1 H, 5.54 (dd, 1 H, J, 6.7, 15.5 Hz, 5.26 (dd, 1 H, J, 9.4, 17.6 Hz, 4.60 (dd, 1 H, J, 3.6, 9.4 Hz, 4.27 (dd, 1 H, J, 3.1, 17.6 Hz, 4.03 (d, 1 H, J, 11.3 Hz, 3.28 (t, 1 H, J, 10.5 Hz, 2.85 (dd, 1 H, J, 9.9, 16.3 Hz, 2.67-2.75 (m, 3 H, 2.37-2.46 (m, 2 H, 2.06-2.14 (m, 1 H, 1.86 (s, 3 H, 1.32 (s, 9 H, 0.68 (d, 3 H, J, 6.9 Hz, 0.53 (d, 3 H, J, 6.9 Hz, 13C NMR (125 MHz, CDCl3, δ, 173.5, 169.3, 168.8, 167.9, 164.5, 147.4, 132.8, 128.1, 124.1, 84.3, 71.9, 57.7, 47.8, 43.2, 41.0, 40.4, 39.4, 34.0, 31.8, 29.9, 24.1, 18.8, 16.6. ESI-MS: m/z, 585.17 (100.0, 607.15 88.8, ESI-HRMS
- +: 585.1689.

54
- 52949091825
- Procedure for the Synthesis of Largazole (1) Compound 20 (9.9 mg, 0.02 mmol) was dissolved in degassed THF-H2O (v/v, 4:1, 2 mL) and treated with n- Bu3P (6.1 mg, 0.03 mmol) at r.t. for 6 h. The reaction solution was made up to 50 mL with EtOAc and dried over anhyd Na2SO4. The free thiol intermediate was obtained after removal of solvent in vacuo. The thiol intermediate was then dissolved in CH2Cl2 (5 mL, DIPEA (21.9 mg, 0.17 mmol, and octanoyl chloride (22 mg, 0.136 mmol) was added at 0°C followed by a catalytic quantity of DMAP. The reaction mixture was stirred at r.t. for 10 min and then quenched by sat. NaHCO3 (5 mL, CH2Cl2 (3 x 30 mL) was used for extraction. The combined organic phases were dried over anhyd Na2SO4 and concentrated in vacuo to give the crude product. Purification with chromatography on SiO2, using EtOAc-hex
- +.

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