Total Syntheses of (+)-Pestaphthalide A and (-)-Pestaphthalide B

Abstract

Total syntheses of (+)-pestaphthalide A and (-)-pestaphthalide B were achieved. Key steps are an iridium-mediated meta-selective arylborylation, a Suzuki-coupling/Jacobsen-epoxidation sequence, a stereodivergent epoxide opening and an anionic cyclic carbonate/γ-lactone rearrangement.

arylborylation - cyclic carbonate/γ-lactone rearrangement - natural products - total synthesis - pestaphthalide A and B

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13

The crystal data of compound rac-19 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 831699. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: [phone]; E-mail: [e-mail]] or via www.ccdc.cam.ac.uk/data_request/cif. Crystal data: C₁₃H₁₆O₅, M = 252.26, triclinic, P1, a = 8.5193 (5) Å, b = 9.3779 (7) Å, c = 9.4830 (6) Å, α = 62.355 (5)˚, β = 66.112 (5)˚, γ = 67.335 (5)˚, V = 595.13 (7) Å^³, Z = 2, D_calcd = 1.408 Mg/m^³, 6344 reflections collected, 2500 independent (R _int = 0.0306), R1 = 0.0325, wR2 = 0.0791 (all data).