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. Author manuscript; available in PMC: 2018 May 31.
Published in final edited form as: J Am Chem Soc. 2017 May 17;139(21):7188–7191. doi: 10.1021/jacs.7b03879

Scheme 1. Diverted Total Synthesis of Carolacton Analogsa.

Scheme 1

a(a) K2CO3, MeOH/THF, >99% (b) DMSO, (COCl)2, CH2Cl2, 94% (c) CuCN, Allyl-MgBr, THF, 90% (d) 4 Å MS, NaOH, PhMe, 83– 85% (e) EDCI, DMAP, CH2Cl2, 89–96% (f) Grubbs 2nd generation catalyst, CH2Cl2, 78–99% (g) Pd/C, H2, 55-69% (h) TBAF, 64–94% (i) HCl, THF/MeOH, 50–82% (j) DMSO, SO3·pyr, CH2Cl2, 63–89% (k) t-BuOH, 2-methyl-2-butene, NaH2PO4, NaClO2, MeCN, H2O, 65-96% (l) TFA/H2O, 59–79%.