Tetrahydrofuran Ring Construction through Tandem Iodocyclizations: Synthesis of Hagen’s Gland Lactones, a Pheromone of Idea leuconoe, an Oxylipid, and Related Compounds

U. Nookaraju; Shivam S. Danve; Pradeep Kumar

doi:10.1055/a-2550-1785

Synlett, Table of Contents

Synlett
DOI: 10.1055/a-2550-1785

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Emerging Trends in Organic Chemistry: A Focus on India

Tetrahydrofuran Ring Construction through Tandem Iodocyclizations: Synthesis of Hagen’s Gland Lactones, a Pheromone of Idea leuconoe, an Oxylipid, and Related Compounds

U. Nookaraju

^aDivision of Organic Chemistry, CSIR-NCL (National Chemical Laboratory), Pune 411008, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India

,

Shivam S. Danve

^aDivision of Organic Chemistry, CSIR-NCL (National Chemical Laboratory), Pune 411008, India

,

Pradeep Kumar∗

^aDivision of Organic Chemistry, CSIR-NCL (National Chemical Laboratory), Pune 411008, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India

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Abstract

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Dedicated to Professor Richard R. Schmidt on the occasion of his 90^th birthday

Abstract

A simple and efficient common route was developed for the syntheses of tetrahydrofuran-ring-containing natural products such as Hagen’s gland lactones and their epimers, a pheromone of the butterfly Idea leuconoe, an oxylipid, and some valuable synthons. Brown’s allylation, cross-metathesis, iodocyclization, and a tandem aminoxylation/allylation were employed as key steps in the syntheses.

Key words

tetrahydrofurans - iodocyclization - Hagen’s gland lactone - oxylipids - pheromones - cross-metathesis

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References

References

1a Zhou Z.-F, Menna M, Cai Y.-S, Guo Y.-W. Chem. Rev. 2015; 115: 1543
1b Bermejo A, Figadère B, Zafra-Polo M.-C, Barrachina I, Estornell E, Cortes D. Nat. Prod. Rep. 2005; 22: 269
1c Rupprecht JK, Hui YH, McLaughlin JL. J. Nat. Prod. 1990; 53: 237
1d Alali FQ, Liu X.-X, McLaughlin JL. J. Nat. Prod. 1999; 62: 504

2a Lorente A, Lamariano-Merketegi J, Albericio F, Álvarez M. Chem. Rev. 2013; 113: 4567
2b Li N, Shi Z, Tang Y, Chen J, Li X. Beilstein J. Org. Chem. 2008; 4: 48
2c Jalce G, Franck X, Figadère B. Tetrahedron: Asymmetry 2009; 20: 2537
2d Wolfe JP, Hay MB. Tetrahedron 2007; 63: 261

3a Hagen KL. Proc. Hawaii. Entomol. Soc. 1953; 15: 115
3b Williams HJ, Wong M, Wharton RA, Vinson SB. J. Chem. Ecol. 1988; 14: 1727
3c Buckingham GR. Ann. Entomol. Soc. Am. 1968; 61: 233

4a Paddon-Jones GC, McErlean CS. P, Hayes P, Moore CJ, König WA, Kitching WA. J. Org. Chem. 2001; 66: 7487
4b Gadikota RR, Callam CS, Lowary TL. J. Org. Chem. 2001; 66: 9046
4c Boukouvalas J, Fortier G, Radu II. J. Org. Chem. 1998; 63: 916
4d Lee E, Yoo S.-K, Choo Y.-S, Cheon H.-S, Chong YH. Tetrahedron Lett. 1997; 38: 7757
4e Osumi KH, Sugimura K. Tetrahedron Lett. 1995; 36: 5789

5a Paddon-Jones GC, Moore CJ, Brecknell DJ, König WA, Kitching W. Tetrahedron Lett. 1997; 38: 3479
5b Mereyala HB, Gadikota RR. Chem. Lett. 1999; 273
5c Mereyala HB, Gadikota RR. Tetrahedron: Asymmetry 2000; 11: 743
5d Mereyala HB, Gadikota RR, Sunder KS, Shailaja S. Tetrahedron 2000; 56: 3021
5e Banda G, Chakravarthy IE. Tetrahedron: Asymmetry 2006; 17: 1684
5f Agrawal D, Sriramurthy V, Yadav VK. Tetrahedron Lett. 2006; 47: 7615
5g Paz-Morales E, Ruth M, Sartillo-Piscil F. Carbohydr. Res. 2009; 344: 1123
5h Fernandes RA, Pullaiah K. J. Org. Chem. 2012; 77: 9357
5i Chaudhari DA, Kattanguru P, Fernandes RA. Tetrahedron: Asymmetry 2014; 25: 1022
5j Gharpure SJ, Nanda LN, Shukla MK. Eur. J. Org. Chem. 2011; 6632
5k Roy A, Bhat BA, Lepore SD. Org. Lett. 2015; 17: 900
5l Kauloorkar S, Jha V, Jogdand G, Kumar P. RSC Adv. 2015; 5: 61000
5m Chowhan LR, Singh V, Lakshmi SR. ChemistrySelect 2019; 4: 13601
5n Lee DI, Shin D, Hwang Y, Lee K, Seoand S.-Y, Kim H. RSC Adv. 2014; 4: 52637
5o Lone AM, Bhat BA, Shah WA, Mehta G. Tetrahedron Lett. 2014; 55: 3610

6a Brown HC, Jadhav PK. J. Am. Chem. Soc. 1983; 105: 2092
6b Racherla US, Brown HC. J. Org. Chem. 1991; 56: 401
6c Ramachandran PV, Reddy MV. R, Brown HC. Tetrahedron Lett. 2000; 41: 583

7a Chatterjee AK, Choi T.-L, Sanders DP, Grubbs RH. J. Am. Chem. Soc. 2003; 125: 11360
7b Hoveyda AH, Lombardi PJ, O’Brien RV, Zhugralin AR. J. Am. Chem. Soc. 2009; 131: 8378
7c Connon SJ, Blechert S. Angew. Chem. Int. Ed. 2003; 42: 1900

8a Kundooru S, Das P, Meena S, Kumar V, Siddiqi MI, Datta D, Shaw AK. Org. Biomol. Chem. 2015; 13: 8241
8b Bedford SB, Bell KE, Bennett F, Hayes CJ, Knight DW, Shaw DE. J. Chem. Soc., Perkin Trans. 1 1999; 2143
8c Ajoy BK, Manuel SL, Elvia CV. C. Curr. Org. Chem. 2011; 15: 1058
8d Mphahlele MJ. Molecules 2009; 14: 4814
8e Snider BB, Johnston M. Tetrahedron Lett. 1985; 26: 5497

9 Mori N, Togo H. Tetrahedron 2005; 61: 5915

10a Tiecco M, Testaferri L, Tingoli M, Bagnoli L, Santi C. Synlett 1993; 798
10b Liu H, Tan C.-H. Tetrahedron Lett. 2007; 48: 8220
10c Bajracharya GB, Koranne PS, Nadaf RN, Mohamed Gabr RK, Takenaka K, Takizawa S, Sasai H. Chem. Commun. 2010; 46: 9064 ; and references cited therein

11a Schulz S, Nishida R. Bioorg. Med. Chem. 1996; 4: 341
11b Schulz S. Chem. Commun. 1999; 1239
11c Kondekar NB, Kumar P. Org. Lett. 2009; 11: 2611
11d Yadav JS, Narayana Reddy PA, Ather H, Suman Kumar A, Prasad AR, Subba Reddy BV, Khazim AA. Synthesis 2012; 44: 579

12a Phae-nok S, Kuhakarn C, Pohmakotr M, Reutrakul V, Soorukram D. Org. Biomol. Chem. 2015; 13: 11087
12b Schulz S, Hötling S. Nat. Prod. Rep. 2015; 32: 1042
12c Browne DM, Niyomura O, Wirth T. Org. Lett. 2007; 9: 3169

13 Zhong G. Chem. Commun. 2004; 606
14 Kim S.-G. Synthesis 2009; 2418

15a García C, Martín T, Martín VS. J. Org. Chem. 2001; 66: 1420
15b Roy S, Spilling CD. Org. Lett. 2012; 14: 2230 ; and references cited therein

16 Fernandes RA, Pathare RS, Gorve DA. Chem. Asian J. 2020; 15: 2815
17 Singh AA, Rowley JA, Schwartz BD, Kitching W, De Voss JJ. J. Org. Chem. 2014; 79: 7799
18 Nookaraju U, Kumar P. RSC Adv. 2015; 5: 63311
19 Fernandes RA, Gorve DA, Jha AK. Chem. Commun. 2023; 59: 2007
20 (3aR,5R,6aR)-5-Butyltetrahydrofuro[3,2-b]furan-2(3H)-one (1) NaHCO₃ (135 mg, 1.61 mmol, 3.0 equiv) and I₂ (204 mg, 1.61 mmol, 3.0 equiv) were sequentially added to a solution of 13a (100 mg, 0.54 mmol) in MeCN (10 mL) at 0 °C, and the mixture was stirred for 6 h then cooled to rt. The reaction was quenched with aq Na₂S₂O₃, and the aqueous layer was extracted with EtOAc (2 × 5 mL). The combined organic layers were washed with H₂O and brine, dried (Na₂SO₄), and concentrated. The residue was purified by column chromatography [silica gel, PE–EtOAc (85:15)] to give a colorless oil; yield: 82.1 mg (83%). [Further elution (PE–EtOAc, 84:16) gave the epimer 3; yield: 6.9 mg (7%)]; [α]_D ²⁵ +49.5 (c 1.0, CHCl₃) [Lit.^5g +50.9 (c 1.0, CHCl₃)]. IR (neat): 2930, 2864, 1781, 1459, 1345, 1180, 1065 cm^–1. ¹H NMR (200 MHz, CDCl₃): δ = 5.13 (t, J = 4.7 Hz, 1 H), 4.84–4.79 (m, 1 H), 4.07 (dt, J = 6.3, 10.8 Hz, 1 H), 2.77 (dd, J = 6.6, 18.8 Hz, 1 H), 2.65 (d, J = 18.6 Hz, 1 H), 2.38 (dd, J = 4.6, 13.7 Hz, 1 H), 1.71–1.65 (m, 1 H), 1.57–1.43 (m, 2 H), 1.43–1.29 (m, 4 H), 0.90 (t, J = 7.0 Hz, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 176.1, 84.9, 78.2, 77.3, 38.8, 36.6, 34.3, 28.1, 22.6, 13.9. HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₀H₁₆NaO₃: 207.0992; found: 207.0994.

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