학술논문

An Enyne Metathesis/(4 + 2)- Dimerization Route to (±)-Differolide

Document Type

Article

Author

Hoye, T. R.; Donaldson, S. M.; Vos, T. J.

Source

Organic Letters; July 1999, Vol. 1 Issue: 2 p277-280, 4p

Subject

Language

ISSN

15237060; 15237052

Abstract

A concise total synthesis of (±)-differolide (1) has been achieved. 2-Vinylbutenolide (2) was prepared by enyne metathesis of allyl propynoate (3) using the Grubbs initiator 4. This reaction was examined by ¹H NMR spectroscopy, which led to the hypothesis that low concentration of ruthenium species and high concentration of enyne substrate would be advantageous. Accordingly, slow addition of 4 to solutions of enyne 3 was found to be beneficial. Spontaneous dimerization of 2 gave (±)-differolide (1) and an isomer.

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