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. Author manuscript; available in PMC: 2010 Dec 2.
Published in final edited form as: J Am Chem Soc. 2009 Dec 2;131(47):17087–17089. doi: 10.1021/ja907924j

Scheme 7. Completion of the synthesis of laulimalide and a potent analoguea.

Scheme 7

aConditions: (a) O3ReOSiPh3, Et2O, 5 min, 78% (97% brsm); (b) Dess-Martin periodinane, CH2Cl2; (c) (R)-Me-CBS, BH3·THF, THF, 93% over 2 steps; (d) (+)-DET, Ti(i-OPr)4, TBHP, 4 Å MS, CH2Cl2, 88%; (e) DDQ, CH2Cl2/pH7 buffer/tert-BuOH, 89%; (f) (+)-DET, Ti(i-OPr)4, TBHP, 4 Å MS, CH2Cl2, 86%; (e) DDQ, CH2Cl2/pH7 buffer/tert-BuOH, 71%.