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Synlett 2013; 24(12): 1545-1548
DOI: 10.1055/s-0033-1338961
DOI: 10.1055/s-0033-1338961
letter
Synthesis of (S,5Z,8E,10E)-12-Hydroxyheptadeca-5,8,10-trienoic Acid (12S-HHT) and its Analogues
Weitere Informationen
Publikationsverlauf
Received: 09. April 2013
Accepted after revision: 10. Mai 2013
Publikationsdatum:
14. Juni 2013 (online)
Abstract
Natural 12S-HHT and its analogues were synthesized for study of structure and activity relationship toward the BLT2 receptor. The Suzuki–Miyaura coupling was used for construction of the 8E,10E-diene moiety of 12S-HHT and analogues of (12R)- and 12-keto-types, whereas Wittig reaction was used for the synthesis of (8Z)- and (8Z,12R)-isomers.
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References and Notes
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- 13 The Noyori reduction of acetylene ketone i afforded alcohol ii with 96% ee by chiral HPLC of the derived benzoate. However, hydrostannation of the TBDPS ether iii under radical- (AIBN) or PdCl2(PPh3)2-catalyzed conditions followed by iodination gave a mixture of (S)-7, the cis-isomer, and the regioisomer (Scheme 3).
- 14 12S-HHT (1): 1H NMR (300 MHz, CDCl3): δ = 0.90 (t, J = 7.0 Hz, 3 H), 1.14–1.80 (m, 10 H), 2.00–2.20 (m, 2 H), 2.37 (t, J = 7.5 Hz, 2 H), 2.83 (t, J = 6.0 Hz, 2 H), 2.60–4.00 (br s, 2 H), 4.12 (q, J = 6.0 Hz, 1 H), 5.30–5.52 (m, 2 H), 5.55–5.73 (m, 2 H), 6.04 (dd, J = 15.0, 10.5 Hz, 1 H), 6.18 (dd, J = 15.0, 10.5 Hz, 1 H). (8Z)-Isomer 3: 1H NMR (300 MHz, CDCl3): δ = 0.91 (t, J = 7.0 Hz, 3 H), 1.18–1.81 (m, 10 H), 2.00–2.26 (m, 2 H), 2.36 (t, J = 7.0 Hz, 2 H), 2.87 (dt, J = 16.0, 7.0 Hz, 1 H), 3.03 (dt, J = 16.0, 7.0 Hz, 1 H), 3.20–4.00 (br s, 2 H), 4.26 (q, J = 6.0 Hz, 1 H), 5.32–5.52 (m, 3 H), 5.69 (dd, J = 15.0, 6.0 Hz, 1 H), 5.98 (t, J = 11.0 Hz, 1 H), 6.58 (dd, J = 15.0, 11.0 Hz, 1 H). 12-Keto isomer 5: 1H NMR (300 MHz, CDCl3): δ = 0.91 (t, J = 7.0 Hz, 3 H), 1.23–1.42 (m, 5 H), 1.57–1.82 (m, 4 H), 2.08–2.22 (m, 2 H), 2.38 (t, J = 7.0 Hz, 2 H), 2.55 (t, J = 7.5 Hz, 2 H), 2.94 (t, J = 5.0 Hz, 2 H), 5.40–5.55 (m, 2 H), 6.05–6.26 (m, 3 H), 7.13 (dd, J = 16.0, 10.0 Hz, 1 H).