Synthesis of the C1–C17 Segment of Bafilomycin N

Haruka Sato; Seijiro Hosokawa

doi:10.1055/s-0037-1611727

Synlett, Table of Contents

Synlett 2019; 30(05): 577-580
DOI: 10.1055/s-0037-1611727

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Synthesis of the C1–C17 Segment of Bafilomycin N

Haruka Sato

,

Seijiro Hosokawa*

Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan Email: seijiro@waseda.jp

› Author Affiliations

Abstract

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Abstract

The C1–C17 segment of bafilomycin N has been synthesized. The C1–C11 segment was synthesized by the anti-selective vinylogous Mukaiyama aldol reaction with a chiral vinylketene silyl N,O-acetal and the Horner–Wadsworth–Emmons reaction, whereas C12–C17 was constructed by the syn-selective vinylogous Mukaiyama aldol reaction and the Jung’s semipinacol rearrangement. Those segments were connected by the Stille coupling to afford the C1–C17 segment.

Key words

bafilomycin - vinylogous Mukaiyama aldol reaction - vinylketene silyl N,O-acetal - polypropionate - semipinacol rearrangement - Stille coupling

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References

References and Notes
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24 Synthesis of C1–C17 Segment 4 To a solution of C1–C11 segment 6 (9.6 mg, 0.0184 mmol) and C12–C17 segment 7 (7.7 mg, 0.0184 mmol) in NMP (0.2 mL) was added LiCl (2.4 mg, 0.0553 mmol, 3.0 equiv) and Pd₂(dba)₃ ·CHCl₃ at rt. After stirring for 4 h, the reaction was diluted with Et₂O (0.2 mL) and H₂O (0.2 mL). The resulting two-phase mixture was filtered through a pad of celite. After the layers had been separated, the aqueous layer was extracted with Et₂O (5 × 0.1 mL). The combined organic layers were dried with Na₂SO₄ and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/EtOAc = 15:1) to give the C1–C17 segment 4 as a yellowish oil (9.4 mg, 0.0154 mmol, 84%). R_f = 0.21 (n-hexane/ethyl acetate = 5:1). [α]_D ²⁰ +46.6 (c 0.28, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 7.11 (s, 1 H), 6.22 (ddd, J = 15.0, 11.0, 1.0 Hz, 1 H), 5.80 (d, J = 10.0 Hz, 1 H), 5.76 (d, J = 11.0 Hz, 1 H), 5.50 (dd, J = 15.0, 9.0 Hz, 1 H), 3.60 (dd, J = 6.5, 3.0 Hz, 1 H), 3.58 (ddd, J = 11.0, 7.0, 5.5 Hz, 1 H), 3.49 (ddd, J = 11.0, 5.5, 5.5 Hz, 1 H), 3.41 (dd, J = 5.0, 3.0 Hz, 1 H), 2.73–2.65 (m, 1 H), 2.40–2.33 (m, 1 H), 2.31–2.25 (m, 1 H), 2.01 (d, J = 1.0 Hz, 3 H), 1.91–1.85 (m, 1 H), 1.84 (d, J = 1.0 Hz, 3 H), 1.80–1.68 (m, 2 H), 1.67 (s, 3 H), 1.00 (d, J = 6.0 Hz, 3 H), 0.98 (d, J = 6.5 Hz, 3 H), 0.91 (s, 9 H), 0.87 (d, J = 7.0 Hz, 3 H), 0.74 (d, J = 6.5 Hz, 3 H), 0.08 (s, TMS, 9 H), 0.05 (s, TBS, 3 H), 0.04 (s, TBS, 3 H) ppm. ¹³C NMR (150 MHz, CDCl₃): δ = 169.8, 143.6, 139.4, 135.5, 135.4, 130.1, 126.7, 126.6, 134.8, 80.2, 77.5, 66.1, 51.8, 43.9, 41.2, 38.8, 36.6, 35.8, 26.12, 26.10, 19.3, 18.4, 18.2, 16.6, 16.3, 15.6, 14.1, 11.0, 0.8, 0.7, –3.77, –3.80 ppm. HRMS (ESI): m/z [M + Na]⁺ calcd for C₃₄H₆₄O₅NaSi₂: 631.4184; found: 631.4179. IR (KBr film): 3469, 2958, 2929, 2857, 1712, 1250, 1117, 1033, 837, 773, 750 cm^–1.

Supplementary Material