Strategies for the Synthesis
of the Cyclopropyl-Substituted Lactone Family of Oxylipins

James D. White; Jongtae Yang

doi:10.1055/s-0029-1217352

ACCOUNT

Strategies for the Synthesis of the Cyclopropyl-Substituted Lactone Family of Oxylipins

James D. White*^a, Jongtae Yang^b
^a Department of Chemisty, Oregon State University, Corvallis, Oregon 97331-4003, USA
e-Mail: james.white@oregonstate.edu;
^b College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, USA

Abstract

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Abstract

Biomimetic and other strategies that have been developed in the author’s laboratory for the synthesis of a subset of the group of enzymically oxidized lipids known as oxylipins are described. This set of oxylipins contains both a cyclopropane and a lactone, with the lactone ring size varying between six and nine members. A biomimetic approach employing cascade cyclization of an epoxyalkenoic acid was successful in creating the cyclopropane and six-membered lactone of C₂₀ oxylipins such as the constanolactones in a single step, but failed in an attempt to create the nine-membered lactone of halicholactone. Solandelactones, C₂₂ oxylipins containing a cyclopropane and an eight-membered lactone, were synthesized by directed Simmons-Smith cyclopropanation followed by Claisen rearrangement of a cyclic ketene acetal to construct the lactone

1 Introduction

2 The First Biomimetic Cascade Synthesis of an Oxylipin

3 Biomimetic Cascade Synthesis of Constanolactones A and B

4 A Failed Biomimetic Strategy for Halicholactone

5 Synthesis of the C₂₂ Oxylipins Solandelactones A, B, E, and F

5.1 A Ring-Closing Metathesis Approach to the Octenalactone Portion of Solandelactones

5.2 The Petasis-Claisen Rearrangement Route to the Octenalactone Portion of Solandelactones

6 Conclusion

Key words

biomimetic synthesis - cascade synthesis - cyclopropanation - Claisen rearrangement - lactones - lipids

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