Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran

Yoo Tanabe; Kumi Mitarai; Takahiro Higashi; Tomonori Misaki; Yoshinori Nishii

doi:10.1039/B208077J

Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran

Yoo Tanabe,*^a Kumi Mitarai,^a Takahiro Higashi,^a Tomonori Misaki^a and Yoshinori Nishii^a

* Corresponding authors

^a Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, Japan
E-mail: tanabe@kwansei.ac.jp

Abstract

TiCl₄–Bu₃N-mediated condensation of ketones with α,α-dimethoxyketones afforded trialkylsubstituted 2(5H)-furanones in a one-pot manner, wherein aldol addition and furanone formation occurred sequentially; its application to straightforward synthesis of (R)-mintlactone and (R)-menthofuran, two representative natural mint perfumes, is demonstrated.

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Publication details

The article was received on 16 Aug 2002, accepted on 13 Sep 2002 and first published on 01 Oct 2002

Article type: Communication

DOI: 10.1039/B208077J

Citation: Chem. Commun., 2002,0, 2542-2543

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Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran

Y. Tanabe, K. Mitarai, T. Higashi, T. Misaki and Y. Nishii, Chem. Commun., 2002, 0, 2542
DOI: 10.1039/B208077J
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Chemical Communications

Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran

Abstract

Supplementary files

Publication details

Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran

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