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. Author manuscript; available in PMC: 2011 Sep 3.
Published in final edited form as: J Org Chem. 2010 Sep 3;75(17):5895–5903. doi: 10.1021/jo101043m

Scheme 1. Synthesis of Polyol/Polyalkyne Scaffold 9a–c.

Scheme 1

aReagents: (a) PBr3, ether (Ref. 12). (b) NaCH(CO2Me)2, EtOH. (c) LiAlH4, ether. (d) disiamyborane, THF; H2O2, NaOH. (e) NaH, Br(CH2)4C≡CH (8). bProduct 7 resulting from anti-Markovnikov hydration is shown. It is assumed that mixtures of all possible stereoisomers of 7 are produced. cStructure 9 is a representative hexaalkyne scaffold. The sites of attachment of the 5-hexyn-1-yl groups shown in 9 are arbitrary.