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(−)-trans-(1a) and (−)-cis-clavicipitic acid (1b). Reagents and conditions: (a) DL-serine, AcOH, Ac2O, 80 °C, 71%; (b) Aspergillus acylase, CoCl2•6H2O, NaH2PO4 buffer, 37 °C, 2 days, 49% (>99% ee); (c) 2-methyl-3-buten-2-ol, Pd(OAc)2 (0.1 equiv.), TPPTS (0.2 equiv.), K2CO3, H2O, 130 °C, 8 h then 60% AcOH (aq), 60 °C, 2 h, 61%.
