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Hoye, T.R. et al.

Hoye, Zhao,

Synthesis of a C(1)-C(14)-containing fragment of callipeltoside A.

[formula: see text] A C(1)-C(14)-containing fragment of callipeltoside A (1, Scheme 1) was synthesized efficiently via a dianion aldol coupling reaction between aldehyde 2 and ketoester 3. A surprising lack of reactivity between the alkenes in 13 and the Grubbs initiator 15 was encountered. An equally surprising rate acceleration of the reaction between 15 and allylic alcohols (alk-1-en-3-ols) as well as their subsequent cleavage to methyl ketones was discovered. In situ 1H NMR analysis has proven to be a very useful tool for monitoring RCM reactions of complex substrates such as 13.[1]

References

Synthesis of a C(1)-C(14)-containing fragment of callipeltoside A. Hoye, T.R., Zhao, H. Org. Lett. (1999) [Pubmed]

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