학술논문

Synthesis of a C(1)−C(14)-Containing Fragment of Callipeltoside A

Document Type

Article

Author

Hoye, T. R.; Zhao, H.

Source

Organic Letters; July 1999, Vol. 1 Issue: 1 p169-172, 4p

Subject

Language

ISSN

15237060; 15237052

Abstract

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.

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