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Synlett 2012; 23(15): 2284-2288
DOI: 10.1055/s-0032-1316994
DOI: 10.1055/s-0032-1316994
letter
Synthesis of the All-l Cyclopentapeptides Versicoloritides A, B, and C
Authors
Further Information
Publication History
Received: 08 June 2012
Accepted: 01 July 2012
Publication Date:
14 August 2012 (online)
Abstract
Herein we describe the first synthesis of the all-l naturally occurring cyclopentapeptides versicoloritides A, B, and C. We found that the extent of oligomerization and epimerization upon head-to-tail cyclization of the linear pentapeptide precursors could be reduced to acceptable levels by modifying the reaction conditions.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information (PDF)
-
References and Notes
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- 13 Versicoloritide B (2) To a solution of DIPEA (28 μL, 161 μmol) in CH2Cl2 (36 mL) was added 5 (18 mg, 32 μmol) and HBTU (36 mg, 95 μmol) in CH2Cl2–DMF (4:1, 15 mL) at 0.5 mL/h. The reaction mixture was concentrated under reduced pressure, diluted with 0.1% TFA–H2O (v/v, 18 mL), and purified by RP-HPLC to afford 2 as a colorless solid (10 mg, 57%). HRMS (EI): m/z [M + Na]+ calcd for C30H35N5NaO5: 568.2536; found: 568.2526. IR: 3277, 2956, 1626, 1542, 1447, 1344, 1162, 746, 702 cm–1. [α]D 20 –46 (c 0.1, MeOH) [lit. –43.6 (c 0.1, MeOH)].1 See the Supporting Information for complete procedures and analytical data
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- 20 Versicoloritide C (3) To a solution of DIPEA (60 μL, 344 μmol) in CH2Cl2 (80 mL) was added 6 (40 mg, 67 μmol) and HBTU (77 mg, 200 μmol) in CH2Cl2–DMF (5:1, 22 mL) at 0.5 mL/h. After complete addition of the reagents, the reaction mixture was concentrated under reduced pressure, diluted with 0.1% TFA–H2O (v/v, 18 mL), and purified by RP-HPLC to afford 3 as a colorless solid (17 mg, 44%). HRMS (EI): m/z [M + Na]+ calcd for C31H37N5NaO6: 598.2642; found: 598.2645. IR: 3307, 2956, 1632, 1523, 1443, 1345, 1165, 746, 700 cm–1. [α]D 20 –135.5 (c 0.2, MeOH) [lit. –118 (c 0.2, MeOH)].1 See Supporting Information for complete procedures and analytical data