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. Author manuscript; available in PMC: 2013 May 7.
Published in final edited form as: Chemistry. 2012 Mar 30;18(19):5826–5831. doi: 10.1002/chem.201200629

Scheme 9.

Scheme 9

Synthesis of unnatural analogue (58). a) In(0), allyl bromide, sat’d aq. NaBr, rt, 16h, 87% (>19:1 dr); b) LiHMDS, 53, DMF, −20 °C to rt, 90%; c) Grubbs II (5 mol%), CH2Cl2, 40 °C, 1 h, 90%; d) TBAF, THF, 0 °C, 95%; e) MnO2, CH2Cl2, 100%; f) i) 44, n-Bu2BOTf, i-PrNEt2, CH2Cl2, −78 °C to rt, ii) TFAA, DMSO, CH2Cl2, −78 °C, 67%; g) i) TFA:H20 (95:5), rt, 45 min; ii) PS-BH(OAc)3, DCE, 49%.