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

James D. White; Jongtae Yang

doi:10.1055/s-0029-1217352

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Synlett 2009(11): 1713-1729
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

Further Information

Publication History

Received 19 December 2008
Publication Date:
12 June 2009 (online)

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

References

1a Gerwick WH. Nagle DG. Proteau PJ. Top. Curr. Chem. 1993, 167: 117

Google Scholar
1b Gerwick WH. Chem. Rev. 1993, 93: 1807

Google Scholar
2 Gerwick WH. Moghaddam MF. Hamberg M. Arch. Biochem. Biophys. 1991, 290: 436

Crossref Google Scholar
3 Gerwick WH. Singh IP. In Lipid Biotechnology Kuo TM. Gardner HW. Marcel Dekker; New York: 2002. p.249-275

Google Scholar
4a Niwa H. Wakamatsu K. Yamada K. Tetrahedron Lett. 1989, 30: 4543

Google Scholar
4b Kigoshi H. Niwa H. Yamada K. Stout TJ. Clardy J. Tetrahedron Lett. 1991, 32: 2427

Google Scholar
5 Higgs MD. Mulheirn LJ. Tetrahedron 1981, 37: 4259

Crossref Google Scholar
6 Corey EJ. De B. Ponder JW. Berg JM. Tetrahedron Lett. 1984, 25: 1015

Crossref Google Scholar
7 Corey EJ. Matsuda SPT. Tetrahedron Lett. 1987, 28: 4247

Crossref Google Scholar
8 Corey EJ. d’Alarcoa M. Matsuda SPT. Lansbury PT. Yamada Y. J. Am. Chem. Soc. 1987, 109: 289

Crossref Google Scholar
9 Brash AR. J. Am. Chem. Soc. 1989, 111: 1891

Crossref Google Scholar
10 Baertschi SW. Brash A. Harris TM. J. Am. Chem. Soc. 1989, 111: 5003

Crossref Google Scholar
11 White JD. Jensen MS. J. Am. Chem. Soc. 1993, 115: 2970

Crossref Google Scholar
12 Jin H. Uenishi J. Christ W. Kishi Y. J. Am. Chem. Soc. 1986, 108: 5644

Google Scholar
13 Gao Y. Hanson R. Klunder J. Ko SY. Sharpless KB. J. Am. Chem. Soc. 1987, 109: 5765

Crossref Google Scholar
14 Takai K. Nitta K. Utimoto K. Masamune H. J. Am. Chem. Soc. 1986, 108: 7408

Crossref Google Scholar
15 Leusink AJ. Budding HA. Drenth W. J. Organomet. Chem. 1968, 11: 541

Crossref Google Scholar
16 Echavarren AM. Tueting DR. Stille JK. J. Am. Chem. Soc. 1988, 110: 4039

Google Scholar
17 Van Tamelen EE. Anderson RJ. J. Am. Chem. Soc. 1972, 94: 8225

Crossref Google Scholar
18 Derome AE. Modern NMR Techniques for Chemistry Research Pergamon; Oxford UK: 1987. p.209-220

Google Scholar
19 Ueno Y. Okawara M. Tetrahedron Lett. 1976, 4597

Crossref Google Scholar
20 Nagle DG. Gerwick WH. Tetrahedron Lett. 1990, 31: 2995

Crossref Google Scholar
21 Nagle DG. Gerwick WH. J. Org. Chem. 1994, 59: 7227

Crossref Google Scholar
22 White JD. Jensen MS. J. Am. Chem. Soc. 1995, 117: 6224

Crossref Google Scholar
23 Leblanc Y. Fitzsimmons BJ. Adams J. Perez F. Rokach J. J. Org. Chem. 1986, 51: 789

Crossref Google Scholar
24 Wong MYH. Gray GR. J. Am. Chem. Soc. 1978, 100: 3548

Crossref Google Scholar
25 Barloy-Da Silva C. Benkouider A. Pale P. Tetrahedron Lett. 2000, 41: 3077

Crossref Google Scholar
26 Yu J. Lai J.-Y. Ye J. Balu N. Reddy LM. Duan W. Fogel ER. Capdevila JH. Falck JR. Tetrahedron Lett. 2002, 43: 3939

Crossref Google Scholar
27 Pietruszka J. Wilhelm T. Synlett 2003, 1698

Article in Thieme Connect Google Scholar
28 On constanolactones C and D, see: Pietruszka J. Rieche ACM. Schöne N. Synlett 2007, 2525

Article in Thieme Connect Google Scholar
On constanolactone E, see:
29a Miyaoka H. Shigemoto T. Yamada Y. Tetrahedron Lett. 1996, 37: 7407

Google Scholar
29b Miyaoka H. Shigemoto T. Yamada Y. Heterocycles 1998, 47: 415

Google Scholar
30 A proposed revision to the absolute configuration of neohalicholactone(54) was found to be in error: Proteau PJ. Rossi JV. Gerwick WH. J. Nat. Prod. 1994, 57: 1717

Crossref PubMed Google Scholar
31 White JD. Jensen MS. Synlett 1996, 31

Article in Thieme Connect Google Scholar
32 Fallis AG. Hearn MTW. Jones ERH. Thaller V. Turner JL. J. Chem. Soc., Perkin Trans. 1 1973, 743

Crossref Google Scholar
33 Gannett PM. Nagel DL. Reilley PJ. Lawson T. Sharpe J. Toth B. J. Org. Chem. 1988, 53: 1064

Crossref Google Scholar
34 Takai K. Kuroda T. Nakatsukasa S. Oshiwa K. Nozaki H. Tetrahedron Lett. 1985, 26: 5585

Crossref Google Scholar
35 Martin GE. Crouch RC. J. Nat. Prod. 1991, 54: 1

Crossref Google Scholar
36 Critcher DJ. Connolly S. Mahon MF. Wills M.
J. Chem. Soc., Chem. Commun. 1995, 139

Crossref Google Scholar
37 Critcher DJ. Connolly S. Wills M. Tetrahedron Lett. 1995, 36: 3763

Crossref Google Scholar
38 Critcher DJ. Connolly S. Wills M. J. Org. Chem. 1997, 62: 6638

Crossref Google Scholar
39a Takemoto Y. Baba Y. Saha G. Nakao S. Iwata C. Tamaka T. Ibuka T. Tetrahedron Lett. 2000, 41: 3653

Google Scholar
39b Baba Y. Saha G. Nakao S. Iwata C. Tanaka T. Ibuka T. Ohishi H. Takemoto Y. J. Org. Chem. 2001, 66: 81

Google Scholar
40 Takahashi T. Watanabe H. Kitahara T. Heterocycles 2002, 58: 99

Crossref Google Scholar
41 Seo Y. Cho KW. Rho J.-R. Shin J. Kwon B.-M. Bok S.-H. Song J.-I. Tetrahedron 1996, 52: 10583

Crossref Google Scholar
42 White JD. Martin WHC. Lincoln CM. Yang J. Org. Lett. 2007, 9: 3481

Crossref Google Scholar
43 White JD. Lincoln CM. Yang J. Martin WHC. Chan DB. J. Org. Chem. 2008, 73: 4139

Crossref PubMed Google Scholar
44 Mohapatra D. Yellol G. Arkivoc 2003, (ix): 21

Google Scholar
45 Lincoln CM. White JD. Yokochi AFT. Chem. Commun. 2004, 2846

Crossref Google Scholar
46 Tamborski CM. Ford FE. Soloski EJ. J. Org. Chem. 1963, 28: 237

Crossref Google Scholar
See:
47a Nagasawa T. Handa Y. Onoguchi Y. Obba S. Suzuki K. Synlett 1995, 739

Google Scholar
47b Nagasawa T. Handa Y. Onoguchi Y. Suzuki K. Bull. Chem. Soc. Jpn. 1996, 69: 31

Google Scholar
47c Taylor RE. Engelhardt FC. Schmitt MJ. Yuan H. J. Am. Chem. Soc. 2001, 123: 2964 ; and references cited therein

Google Scholar
48 Still WC. Gennari C. Tetrahedron Lett. 1983, 24: 4405

Crossref Google Scholar
49a Guz NR. Phillips AJ. Org. Lett. 2002, 4: 2253

Google Scholar
49b Crimmins MT. King BW. Tabet EA. J. Am. Chem. Soc. 1997, 119: 7883

Google Scholar
49c Crimmins MT. King BW. Tabet EA. Chaudhary K. J. Am. Chem. Soc. 2001, 66: 894

Google Scholar
50 Oshima K. Takai K. Hotta Y. Nozaki H. Tetrahedron Lett. 1978, 2417

Crossref Google Scholar
52 Charette AB. Lebel HJ. J. Org. Chem. 1995, 60: 2966

Crossref Google Scholar
53a Petrzilka M. Helv. Chim. Acta 1978, 61: 3075

Google Scholar
53b Baudat R. Petrzilka M. Helv. Chim. Acta 1979, 62: 1406

Google Scholar
54a Robinson RA. Clark JS. Holmes AB. J. Am. Chem. Soc. 1993, 115: 10400

Google Scholar
54b Burton JW. Clark JS. Derrer S. Stork TC. Bendall JG. Holmes AB. J. Am. Chem. Soc. 1997, 119: 7483

Google Scholar
55 Nagao Y. Hagiwara Y. Kumagai T. Ochiai M. Inoue T. Hashimoto K. Fujita E. J. Org. Chem. 1986, 51: 2391

Crossref Google Scholar
56 Vlieghe P. Clerc T. Pannecouque C. Witvrouw M. De Clerq E. Salles JP. Kraus JL. J. Med. Chem. 2001, 44: 3014

Crossref Google Scholar
57 Carling RW. Holmes AB. J. Chem. Soc., Chem. Commun. 1986, 325

Crossref Google Scholar
58 Petasis NA. Bzowej EI. J. Am. Chem. Soc. 1990, 112: 6392

Crossref Google Scholar
59 Anderson EA. Davidson JEP. Harrison JR. O’Sullivan PT. Burton JW. Collins I. Holmes AB. Tetrahedron 2002, 58: 1943

Crossref Google Scholar
60 Saito S. Hasegawa T. Inaba M. Nishida R. Fujii T. Nomizu S. Moriwake T. Chem. Lett. 1984, 1389

Crossref Google Scholar
61 Bessodes M. Komiotis D. Autonakis K. Tetrahedron Lett. 1986, 27: 579

Crossref Google Scholar
62a Davoren JE. Martin SF. J. Am. Chem. Soc. 2007, 129: 510

Google Scholar
62b Davoren JE. Harcken C. Martin SF. J. Org. Chem. 2008, 73: 391

Google Scholar
63 Pietruszka J. Rieche ACM. Adv. Synth. Catal. 2008, 350: 1407

Crossref Google Scholar

51

An ab initio calculation using a Hartree-Fock/6-31G** basis set places the barrier at 7-9 kcal˙mol^-¹