A Stereocontrolled Synthesis of Methyl (-)-Nonactate

Joon Won  Jeong; Byoung Young  Woo; Deok-Chan  Ha; Zaesung  No

doi:10.1055/s-2003-37129

LETTER

A Stereocontrolled Synthesis of Methyl (-)-Nonactate

Joon Won Jeong*^a, Byoung Young Woo^a, Deok-Chan Ha^b, Zaesung No*^a
^a Medicinal Science Division, Korea Research Institute of Chemical Technology, Daejeon 305-343, Korea
Fax: +82(42)8607160; e-Mail: jeongjw@krict.re.kr;
^b Department of Chemistry, Korea University, Seoul 136-701, Korea

Abstract

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Abstract

A stereoselective synthesis of methyl (-)-nonactate is described. (E)-γ-Triethylsilyloxyalkene 13 generated from sulfone 10 and (S)-2-benzyloxypropanal underwent intramolecular iodoetherification in the presence of silver carbonate to provide cis-2,5-disubstituted tetrahydrofuran 8 as a key intermediate.

Key words

asymmetric synthesis - cyclizations - sulfones - nonactic acid - iodoetherifications

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References

<A NAME="RU13002ST-1A">1a</A> Corbaz R. Ettlinger L. Gaumann E. Keller-Schielein W. Kradolfer F. Neipp L. Prelog V. Zähner H. Helv. Chim. Acta 1955, 38: 1445

<A NAME="RU13002ST-1B">1b</A> Dominquez J. Dunitz JD. Gerlach H. Prelog V. Helv. Chim. Acta 1962, 45: 129

<A NAME="RU13002ST-1C">1c</A> Keller-Schielein W. Fortschr. Chem. Org. Naturst. 1968, 26: 161

<A NAME="RU13002ST-1D">1d</A> Keller-Schielein W. Helv. Chim. Acta 1973, 30: 313

<A NAME="RU13002ST-2A">2a</A> Young CC. J. Chem. Educ. 1997, 74: 177

<A NAME="RU13002ST-2B">2b</A> Ghauri MS. Thomas JSR. Analyst 1994, 119: 2323

<A NAME="RU13002ST-3A">3a</A> Lee JY. Kim BH. Tetrahedron 1996, 52: 571 ; and references cited therein

<A NAME="RU13002ST-3B">3b</A> Takatori K. Tanaka K. Matsuoka K. Morishita K. Kajiwara M. Synlett 1997, 159

<A NAME="RU13002ST-3C">3c</A> Ahmar M. Duyck C. Fleming I. J. Chem. Soc., Perkin Trans. 1 1998, 2721

<A NAME="RU13002ST-3D">3d</A> Lee E. Choi SJ. Org. Lett. 1999, 1: 1127

<A NAME="RU13002ST-4A">4a</A> Rychnovsky SD. Bartlett PA. J. Am. Chem. Soc. 1981, 103: 3963

<A NAME="RU13002ST-4B">4b</A> Boivin TLB. Tetrahedron 1987, 43: 3309

<A NAME="RU13002ST-4C">4c</A> Cardillo G. Orena M. Tetrahedron 1990, 46: 3321

<A NAME="RU13002ST-4D">4d</A> Harmange J.-C. Figadere B. Tetrahedron: Asymmetry 1993, 4: 1711

<A NAME="RU13002ST-5A">5a</A> Kang SH. Jeong JW. Hwang YS. Lee SB. Angew. Chem. Int. Ed. 2002, 41: 1392

<A NAME="RU13002ST-5B">5b</A> Kang SH. Jeong JW. Tetrahedron Lett. 2002, 43: 3613

<A NAME="RU13002ST-6">6</A> Roush WR. Hoong LK. Palmer MAJ. Staub JA. Palkowitz AD. J. Org. Chem. 1990, 55: 4117

<A NAME="RU13002ST-7">7</A> Varelis P. Johnson B. Aust. J. Chem. 1995, 48: 1775

<A NAME="RU13002ST-8">8</A> Freemann F. Robarge KD. Tetrahedron Lett. 1985, 26: 1943

<A NAME="RU13002ST-9A">9a</A> Baudin JB. Hareau G. Julia SA. Ruel O. Tetrahedron Lett. 1991, 32: 1175

<A NAME="RU13002ST-9B">9b</A> Blakemore PR. Cole WJ. Kocienski PJ. Morley A. Synlett 1998, 26

Spectral data for 8: ¹H NMR (300 MHz, CDCl₃): δ = 7.34-7.22 (5 H, m), 4.59 (1 H, d, J = 11.6 Hz), 4.47 (1 H, d, J = 11.6 Hz), 4.05-3.95 (1 H, m), 3.78-3.72 (2 H, m), 3.70-3.63 (1 H, m), 3.48 (1 H, dd, J = 9.8 Hz, 6.9 Hz), 1.99-1.82 (2 H, m), 1.78-1.42 (5 H, m), 1.24 (3 H, d, J = 6.2 Hz), 0.89 (9 H, s), 0.88 (3 H, d, J = 6.8 Hz), 0.04 (6 H, s); ¹³C NMR (75 MHz, CDCl₃) δ 139.1, 128.3, 127.7, 127.3, 80.5, 76.0, 73.1, 70.7, 65.7, 44.0, 41.3, 31.6, 28.6, 25.9, 20.4, 18.3, 13.1, -5.4; IR (neat) 1251, 1070, 1028, 1006, 834 cm^-1; HRMS (EI) calcd for C₂₃H₄₀O₅Si: 392.2747, found: 392.2748; [α]_D ²³ = +23.0, c = 1.00, CHCl₃.

<A NAME="RU13002ST-11">11</A> Liu H.-J. Han I.-S. Synth. Commun. 1985, 15: 759

<A NAME="RU13002ST-12">12</A> Takatori K. Tanaka N. Tanaka K. Kajiwara M. Heterocycles 1993, 36: 1489