Stereoselective Synthesis of
Methyl Spongoate, a New Steroid with Potent Antitumor
Activities

Jing-Xu Gong; Ze-Hong Miao; Li-Gong Yao; Jian Ding; Tibor Kurtán; Yue-Wei Guo

doi:10.1055/s-0029-1218567

LETTER

Stereoselective Synthesis of Methyl Spongoate, a New Steroid with Potent Antitumor Activities

Jing-Xu Gong^a, Ze-Hong Miao^a, Li-Gong Yao^a, Jian Ding^a, Tibor Kurtán^b, Yue-Wei Guo*^a
^a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P. R. of China
Fax: +86(21)50805813; e-Mail: ywguo@mail.shcnc.ac.cn;
^b Department of Organic Chemistry, University of Debrecen, PO Box 20, 4010 Debrecen, Hungary

Abstract

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Abstract

The stereoselective synthesis of methyl spongoate, a naturally occurring new steroid derivative with an unusual C-20 methoxycarbonyl group and potent antitumor activities, was achieved starting from the commercially available pregnenolone acetate in 11% overall yield.

Key words

steroids - methyl spongoate - stereoselective synthesis - diastereoselective alkylation - cytotoxicity

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Referenzen

References

<A NAME="RW14109ST-1A">1a</A> Davidson BS. Molinski TF. Barrows LR. Ireland CM. J. Am. Chem. Soc. 1991, 113: 4709

<A NAME="RW14109ST-1B">1b</A> Searle PA. Molinski TF. J. Org. Chem. 1994, 59: 6600

<A NAME="RW14109ST-1C">1c</A> Litaudon M. Trigalo F. Martin MT. Frappier F. Guyot M. Tetrahedron 1994, 50: 5323

<A NAME="RW14109ST-1D">1d</A> Makarieva TN. Stonik VA. Dmitrenok AS. Grebnev BB. Iskov VV. Rebachyk NM. J. Nat. Prod. 1995, 58: 254

<A NAME="RW14109ST-2A">2a</A> Cheng S.-Y. Dai C.-F. Duh C.-Y. Steroids 2007, 72: 573

<A NAME="RW14109ST-2B">2b</A> Duh C.-Y. Lo I.-W. Wang S.-K. Cheng S.-Y. Steroids 2007, 72: 653

<A NAME="RW14109ST-2C">2c</A> Wang S.-K. Dai C.-F. Duh C.-Y. J. Nat. Prod. 2006, 69: 103

<A NAME="RW14109ST-3">3</A> Yan X.-H. Lin L.-P. Ding J. Guo Y.-W. Bioorg. Med. Chem. Lett. 2007, 17: 2661

<A NAME="RW14109ST-4">4</A> Cabaj JE. Kairys D. Benson TR. Org. Process Res. Dev. 2007, 11: 378

<A NAME="RW14109ST-5">5</A> Wicha J. Bal K. J. Chem. Soc., Perkin Trans. 1 1977, 1282

<A NAME="RW14109ST-6">6</A> Lewbart ML. Schneider JJ. J. Org. Chem. 1968, 33: 1707

<A NAME="RW14109ST-7">7</A> Wolfling J. Mernyak E. Sebok M. Schneider G. Collect. Czech. Chem. Commun. 2001, 66: 1831

<A NAME="RW14109ST-8">8</A> Bull JR. J. Chem. Soc., Perkin Trans. 1 1971, 627

<A NAME="RW14109ST-9">9</A> Mappus E. Chambon C. Fenet B. Rolland de Ravel M. Grenot C. Cuilleron CY. Steroids 2000, 65: 459

Characteristic Spectroscopic Data of Compound 8
[α]_D ^²0 +55.0 (c 0.45, CHCl₃). ^¹H NMR (400 MHz, CDCl₃): δ = 3.63 (s, 3 H), 0.98 (s, 3 H), 0.83 (d, J = 6.6 Hz, 3 H), 0.82 (d, J = 6.6 Hz, 3 H), 0.69 (s, 3 H). ^¹³C NMR and DEPT (100 MHz, CDCl₃): δ = 11.0 (CH₃), 12.1 (CH₃), 21.2 (CH₂), 22.3 (CH), 22.7 (CH), 23.7 (CH₂), 25.1 (CH₂), 27.1 (CH₂), 27.8 (CH), 28.8 (CH₂), 31.6, (CH₂), 32.2 (CH₂), 35.3 (CH), 35.6 (C), 37.4 (CH₂), 38.2 (CH₂), 38.8 (CH₂), 42.1 (C), 44.7 (CH₂), 46.6 (CH), 47.3 (CH), 51.0 (CH₃), 52.7 (CH), 53.7 (CH), 55.4 (CH), 176.7 (C), 212.2 (C). HRMS: m/z calcd for C₂₈H₄₆O₃ [M⁺]: 430.3447; found: 430.3435.

<A NAME="RW14109ST-11">11</A> Corey EJ. Schmidt G. Tetrahedron Lett. 1979, 20: 399

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