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. 2004 Jun 16;101(33):11986–11991. doi: 10.1073/pnas.0401548101

Scheme 10.

Scheme 10.

Synthesis of the (7S)-epimer of the revised C5–C16 degradation fragment. Conditions: a, (i) 45, (-)-Ipc2BCl, Et3N, -78°C, Et2O; (ii) 48; b, diethylphosphonoacetic acid, DMAP, Et3N, 2,4,6-trichlorobenzoyl chloride, CH2Cl2, 0°C; c, Ba(OH)2, THF, 0°C; d, O3, MeOH, -78°C; NaBH4, -78°C to rt. †, 500 MHz, CD3OD, δ (ppm). ‡, Isolated as 1:2 mixture of (5S)-54a/(5R)-54b.